Iodobenzene [C6H5I] by Asch

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1037 reactions in Reaxys

2018-06-17 20h:27m:12s (UTC)

Search as: Product, As drawn, No mixtures ) AND (RX.PXRN=1446140)))

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Rx-ID: 1981255 View in Reaxys 1/1037 Yield

Conditions & References With silver tetrafluoroborate, iodine in methanol, Time= 0.5h, T= 0 °C Wilson, Stephen R.; Jacob, Linda A.; Journal of Organic Chemistry; vol. 51; nb. 25; (1986); p. 4833 - 4836 View in Reaxys With silver tetrafluoroborate, iodine in methanol, Time= 0.5h, T= 0 °C , other substituted aryl compounds; other reagents, var. temp., time, Product distribution Wilson, Stephen R.; Jacob, Linda A.; Journal of Organic Chemistry; vol. 51; nb. 25; (1986); p. 4833 - 4836 View in Reaxys With silver trifluoroacetate, Iodine monochloride in methanol, Time= 0.25h, T= 0 °C Jacob; Chen; Stec; Synthesis; nb. 6; (1993); p. 611 - 614 View in Reaxys With silver trifluoroacetate, Iodine monochloride in methanol, Time= 0.25h, T= 0 °C , AgBF4 instead of CF3CO2Ag; other aryltrimethylsilanes Jacob; Chen; Stec; Synthesis; nb. 6; (1993); p. 611 - 614 View in Reaxys With sulfuric acid, potassium iodide in methanol, acetonitrile, T= 20 °C , Electrochemical reaction, Reagent/catalyst, Solvent Möckel, Robert; Hille, Jessica; Winterling, Erik; Weidemüller, Stephan; Faber, Tabea Melanie; Hilt, Gerhard; Angewandte Chemie - International Edition; vol. 57; nb. 2; (2018); p. 442 - 445; Angew. Chem.; vol. 130; nb. 2; (2018); p. 450 454,5 View in Reaxys

-2 (v6) I HH (v6) B (v6) H (v6) BB B H H (v6) BB (v6) (v6) HB B BB (v6) HB(v6) H HH (v6) B (v6) (v6) H

(v6) (v6)

+ (v6) P B–(v6) (v6) H (v6) BH B B BHB H (v6)

P+

B B B (v6) H BH (v6) H HB (v6) – (v6) H B H (v6)

2 P+

Rx-ID: 47360240 View in Reaxys 2/1037 Yield 24.7 %

Conditions & References Time= 18h, T= 180 °C , Inert atmosphere, Pyrolysis Dopke, Joel A.; Lincoln, Zachary S.; Blazejewski, Jacob; Staples, Richard J.; Lee, Mark E.; Inorganica Chimica Acta; vol. 473; (2018); p. 263 - 267 View in Reaxys

Rx-ID: 848952 View in Reaxys 3/1037 Yield

Conditions & References With cobalt(III) acetate, trifluoroacetic acid, potassium iodide in water, Time= 0.00333333h, T= 25 °C , Mn(OAc)3 or (NH4)2Ce(SO4)3 instead Co(OAc)3; object of study: oxidative iodination promoted by Co(III), Ni(III) or Ce(IV)

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Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 1003 - 1006; Zhurnal Organicheskoi Khimii; vol. 22; nb. 6; (1986); p. 1117 - 1120 View in Reaxys With cobalt(III) acetate, trifluoroacetic acid in water, Time= 0.00333333h, T= 25 °C Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 1003 - 1006; Zhurnal Organicheskoi Khimii; vol. 22; nb. 6; (1986); p. 1117 - 1120 View in Reaxys With iodine, silver trifluoromethanesulfonate in dichloromethane, T= 20 °C Mulholland; Zheng; Synthetic Communications; vol. 31; nb. 20; (2001); p. 3059 - 3068 View in Reaxys With potassium permanganate, sulfuric acid, iodine in acetic acid, Time= 2.5h, T= 100 °C Chaikovskii; Novikov; Journal of applied chemistry of the USSR; vol. 57; nb. 1 pt 2; (1984); p. 121 - 123 View in Reaxys With lead(II,IV) oxide, trifluoroacetic acid, potassium iodide, T= 20 °C , reagents ratio, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Serguchev, Yu. A.; Davydova, V. G.; Beletskaya, I. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 11; (1987); p. 2424 - 2426; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1987); p. 2609 - 2611 View in Reaxys With potassium bromate, hydrogenchloride, potassium iodide in water, acetic acid, Time= 3h, T= 80 °C Sathiyapriya; Karunakaran, R. Joel; Journal of Chemical Research; nb. 9; (2006); p. 575 - 576 View in Reaxys With N-iodo-succinimide, iron(III) chloride in acetonitrile, Time= 5h, T= 100 °C Tanemura, Kiyoshi; Suzuki, Tsuneo; Nishida, Yoko; Satsumabayashi, Koko; Horaguchi, Takaaki; Chemistry Letters; vol. 32; nb. 10; (2003); p. 932 - 933 View in Reaxys With Oxone, sodium iodide in water, Time= 6h, Reflux Firouzabadi; Iranpoor; Kazemi; Canadian Journal of Chemistry; vol. 87; nb. 12; (2009); p. 1675 - 1681 View in Reaxys With trifluorormethanesulfonic acid, [bis(pyridine)iodine]+ tetrafluoroborate in dichloromethane, Time= 1h, Ambient temperature Barluenga; Gonzalez; Garcia-Martin; Campos; Tetrahedron Letters; vol. 34; nb. 24; (1993); p. 3893 - 3896 View in Reaxys With trifluorormethanesulfonic acid, [bis(pyridine)iodine]+ tetrafluoroborate in dichloromethane, Time= 2h, Ambient temperature Barluenga, Jose; Gonzalez, Jose M.; Garcia-Martin, Miguel A.; Campos, Pedro J.; Asensio, Gregorio; Journal of Organic Chemistry; vol. 58; nb. 8; (1993); p. 2058 - 2060 View in Reaxys With cerium(III) chloride heptahydrate, dihydrogen peroxide, sodium iodide in water, Time= 6h, Reflux, regioselective reaction Firouzabadi, Habib; Iranpoor, Nasser; Kazemi, Somayeh; Ghaderi, Arash; Garzan, Atefeh; Advanced Synthesis and Catalysis; vol. 351; nb. 11-12; (2009); p. 1925 - 1932 View in Reaxys With sodium peroxide, hydrogen iodide in acetic acid, Time= 2h, T= 78 - 80 °C Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys

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With sulfuric acid, iodine, oxygen, nitric acid in water, Time= 6h, T= 29.9 - 49.9 °C , p= 750.06Torr , Rate constant Dorfman; Aleshkova; Russian Journal of Organic Chemistry; vol. 33; nb. 11; (1997); p. 1585 - 1597 View in Reaxys With silver(II) sulfate, iodine, silver trifluoromethanesulfonate in dichloromethane, Time= 1h, Ambient temperature Sekher, Padmanabhan; Gano, James E.; Luzik Jr., Eddie D.; Synthetic Communications; vol. 27; nb. 20; (1997); p. 3631 3636 View in Reaxys With sodium dodecyl-sulfate, sodium iodide, Ce(OH)3OOH, Time= 3h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Garzan, Atefeh; Advanced Synthesis and Catalysis; vol. 347; nb. 15; (2005); p. 1925 1928 View in Reaxys With iodine, copper dichloride, aluminium trichloride, Time= 2h, T= 40 °C Sugita, Toshio; Idei, Mitsushige; Ishibashi, Yoshiyuki; Takegami, Yoshinobu; Chemistry Letters; (1982); p. 1481 - 1484 View in Reaxys With ammonium iodide, oxygen, nitrosonium tetrafluoroborate, trifluoroacetic anhydride in trifluoroacetic acid, Time= 50h, T= 25 °C Radner, Finn; Journal of Organic Chemistry; vol. 53; nb. 15; (1988); p. 3548 - 3553 View in Reaxys With chromium(VI) oxide, sulfuric acid, iodine in acetic anhydride, acetic acid, Time= 1h, T= 55 - 65 °C , Iodination Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 70; nb. 7; (1997); p. 1665 - 1669 View in Reaxys With thallium (III) oxide, potassium iodide in trifluoroacetic acid, Ambient temperature Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 67; nb. 4; (1997); p. 654 - 655; Zhurnal Obshchei Khimii; vol. 67; nb. 4; (1997); p. 699 - 700 View in Reaxys With iodine, dinitrogen tetraoxide, pyrographite, ferric nitrate, Time= 24h, T= 20 °C Firouzabadi; Iranpoor; Shiri; Tetrahedron Letters; vol. 44; nb. 49; (2003); p. 8781 - 8785 View in Reaxys With iodine, bis-[(trifluoroacetoxy)iodo]benzene in tetrachloromethane, Time= 0.3h, Ambient temperature Merkushev, E. B.; Yudina, N. D.; Journal of Organic Chemistry USSR (English Translation); vol. 17; (1981); p. 2320 - 2322; Zhurnal Organicheskoi Khimii; vol. 17; nb. 12; (1981); p. 2598 - 2601 View in Reaxys With N-iodo-succinimide, trifluoroacetic acid, Time= 1h, T= 20 °C , regioselective reaction Bergström, Maria; Suresh, Ganji; Naidu, Veluru Ramesh; Unelius, C. Rikard; European Journal of Organic Chemistry; vol. 2017; nb. 22; (2017); p. 3234 - 3239 View in Reaxys With dioxochloro(trimethylsiloxy)chromate(VI), iodine in dichloromethane, Time= 5h, Ambient temperature Aizpurua, J. M.; Juaristi, M.; Lecea, B.; Palomo, C.; Tetrahedron; vol. 41; nb. 14; (1985); p. 2903 - 2912 View in Reaxys With sodium periodate, sulfuric acid, iodine in acetic anhydride, acetic acid, Time= 4h, T= 20 °C , Iodination Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 73; nb. 4; (2000); p. 951 - 956 View in Reaxys With manganese(IV) oxide, sulfuric acid, iodine, acetic anhydride in acetic acid, 1.) room temperature, 2 h, 2.) 45-55 deg C, 2 h, 3.) room temperature, overnight

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Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 72; nb. 1; (1999); p. 115 - 120 View in Reaxys With iodine, lithium perchlorate in various solvent(s), Ambient temperature, anodic oxidation Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Ikeda, Kaoru; Kamada, Tohru; Tetrahedron Letters; vol. 30; nb. 13; (1989); p. 1649 - 1650 View in Reaxys With tetraiodoglycoluril, sulfuric acid in 1,4-dioxane, Time= 0.333333h, T= 20 °C Chaikovski; Filimonov; Yagovkin; Ogorodnikov; Russian Chemical Bulletin; vol. 50; nb. 12; (2001); p. 2411 - 2415 View in Reaxys With manganese(IV) oxide, sulfuric acid, iodine in acetic anhydride, acetic acid, Time= 2h, T= 70 °C Lulinski, Piotr; Krassowska-Swiebocka, Barbara; Skulski, Lech; Molecules; vol. 9; nb. 7; (2004); p. 595 - 601 View in Reaxys With tetrafluoroboric acid, iodine, mercury(II) oxide in dichloromethane, Time= 4h, Ambient temperature Barluenga, Jose; Campos, Pedro J.; Gonzalez, Jose M.; Asensio, Gregorio; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1984); p. 2623 - 2624 View in Reaxys With iodine, mercury(II) nitrate in dichloromethane, Time= 14h, T= 20 °C , reactions of derivatives with var. mercury(II)-salts, Product distribution Bachki, Abderrazak; Foubelo, Francisco; Yus, Miguel; Tetrahedron; vol. 50; nb. 17; (1994); p. 5139 - 5146 View in Reaxys With iodine, mercury(II) nitrate in dichloromethane, Time= 14h, T= 20 °C Bachki, Abderrazak; Foubelo, Francisco; Yus, Miguel; Tetrahedron; vol. 50; nb. 17; (1994); p. 5139 - 5146 View in Reaxys With sulfuric acid, iodine, acetic anhydride in acetic acid, Time= 0.25h, T= 20 °C , oxidative iodination Kryska, Anna; Skulski, Lech; Journal of Chemical Research, Miniprint; nb. 10; (1999); p. 2501 - 2517 View in Reaxys With IPy2BF4*2HBF4 in dichloromethane, Ambient temperature Barluenga, Jose; Gonzalez, Jose M.; Garcia-Martin, Miguel A.; Campos, Pedro J.; Asensio, Gregorio; Journal of the Chemical Society, Chemical Communications; nb. 14; (1992); p. 1016 - 1017 View in Reaxys With dihydrogen peroxide, iodine, acetic anhydride, urea, sulfuric acid in acetic acid, T= 10 - 15 °C Lulinski, Piotr; Kryska, Anna; Sosnowski, Maciej; Skulski, Lech; Synthesis; nb. 3; (2004); p. 441 - 445 View in Reaxys With sodium percarbonate, sulfuric acid, iodine, acetic anhydride, acetic acid, Time= 2h, T= 45 - 50 °C Zielinska, Agnieszka; Skulski, Lech; Molecules; vol. 10; nb. 10; (2005); p. 1307 - 1317 View in Reaxys With bismuth(III) nitrate, iodine, silica gel, Time= 72h, T= 20 °C Alexander, Varughese M.; Khandekar, Amit C.; Samant, Shriniwas D.; Synlett; nb. 12; (2003); p. 1895 - 1897 View in Reaxys With dicloroiodoisocyanuric acid in acetonitrile, Time= 1608h, T= 20 °C , Darkness, regioselective reaction Da Silva Ribeiro, Rodrigo; Esteves, Pierre M.; De Mattos, Marcio C.S.; Journal of the Brazilian Chemical Society; vol. 23; nb. 2; (2012); p. 228 - 235 View in Reaxys

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With aluminum oxide, iodine in solid, Time= 20h, Ambient temperature Boothe, Richard; Dial, Christopher; Conaway, Richard; Pagni, Richard M.; Kabalka, George W.; Tetrahedron Letters; vol. 27; nb. 20; (1986); p. 2207 - 2210 View in Reaxys With silver(I) nitrite, iodine in dichloromethane, Time= 72h, Ambient temperature, investigation of iodination of var. alkylbenzenes, Product distribution Sy, Wing-Wah; Lodge, Bruce A.; Tetrahedron Letters; vol. 30; nb. 29; (1989); p. 3769 - 3772 View in Reaxys With iodine, Time= 20h, T= 22 °C , other aromatic hydrocarbons, alkenes, alkynes; var. temperatur, time, reagents, Product distribution, Mechanism Pagni, Richard M.; Kabalka, George W.; Boothe, Richard; Gaetano, Kevan; Stewart, Lyman J.; et al.; Journal of Organic Chemistry; vol. 53; nb. 19; (1988); p. 4477 - 4482 View in Reaxys With iodine, fluorine in chloroform, trichlorofluoromethane, Time= 24h, T= -78 °C , other aromatic compounds Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys With aluminum oxide, iodine, Time= 20h, investigations of the influence of the factors (reaction time, reaction temperature and the extent of dehydration of the alumina) to the product yields, Product distribution Boothe, Richard; Dial, Christopher; Conaway, Richard; Pagni, Richard M.; Kabalka, George W.; Tetrahedron Letters; vol. 27; nb. 20; (1986); p. 2207 - 2210 View in Reaxys With Pb4(OAc)4, iodine, trifluoroacetic acid, prototype reaction, oth. benzene derivatives, oth. reagent (alkali-metal iodide), intermediate, Rate constant Serguchev, Yu. A.; Davydova, V. G.; Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 9; (1985); p. 1841; Zhurnal Organicheskoi Khimii; vol. 21; nb. 9; (1985); p. 2010 2011 View in Reaxys With silver salt, iodine Birckenbach; Goubeau; Berninger; Chemische Berichte; vol. 65; (1932); p. 1339,1343 View in Reaxys Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys With iodine, nitric acid Roedig; ; vol. 5/4; (1960); p. 573 View in Reaxys Dains; Brewster; ; Vol. I <2. Ausg. 1941> 323 View in Reaxys With sulfuric acid, iodine, nitric acid, acetic acid Varma; Sreenivasmurthyachar; Journal of the Indian Chemical Society; vol. 13; (1936); p. 187 View in Reaxys With ammonium peroxydisulfate, iodine, sodium acetate Marko; Beljajew; ; vol. 3; nb. 4; (1939); p. 3; ; (1943); p. 6250 View in Reaxys With iodine, copper dichloride

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Marko; Beljajew; ; vol. 3; nb. 4; (1939); p. 3; ; (1943); p. 6250 View in Reaxys With iodine, silver sulfate Marko; Beljajew; ; vol. 3; nb. 4; (1939); p. 3; ; (1943); p. 6250 View in Reaxys With sulfuric acid, iodine, nitric acid, acetic acid Nowikow; Zhurnal Obshchei Khimii; vol. 24; (1954); p. 655; engl. Ausg. S. 665 View in Reaxys With iodine, silver trifluoroacetate Haszeldine; Sharpe; Journal of the Chemical Society; (1952); p. 993,1000 View in Reaxys With nitrosulfuric acid, acetic acid, durch Jodierung Varma; Kulkarni; ; vol. 3; p. 294; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 1432 View in Reaxys With sulfuric acid, acetic acid, sodium nitrite, durch Jodierung Varma; Panikar; ; vol. 3; p. 343; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 1432 View in Reaxys With potassium iodate, sulfuric acid Peltzer; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 201 View in Reaxys With sulfuric acid, iodine Istrati; Georgescu; Chemiker-Zeitung, Chemische Apparatur; vol. 1; p. 56; 16 Repert. <1892>, 102 View in Reaxys Istrati; Bulletin de la Societe Chimique de France; vol. <3> 5; (1891); p. 159; ; vol. 1; p. 17 View in Reaxys Neumann; Justus Liebigs Annalen der Chemie; vol. 241; (1887); p. 84 View in Reaxys With iodine, iron(III) chloride, T= 100 °C Meyer,L.; Justus Liebigs Annalen der Chemie; vol. 231; (1885); p. 195; Journal fuer Praktische Chemie (Leipzig); vol. <2> 34; (1886); p. 504 View in Reaxys With aluminium trichloride, Iodine monochloride Greene; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 90; (1880); p. 41 View in Reaxys With sodium persulfate, iodine, acetic acid Elbs; Jaroslawzew; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 92 View in Reaxys With iodine, nitric acid, T= 50 °C Datta; Chatterjee; Journal of the American Chemical Society; vol. 39; (1917); p. 437 View in Reaxys Organic Synthesees; View in Reaxys With iodic acid Peltzer; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 201

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View in Reaxys With iodosulfur, nitric acid Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys Patent; Kalle and Co.; DE123746 View in Reaxys With iodine, fluorine in chloroform, trichlorofluoromethane, Time= 24h, T= -78 °C , Yield given Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys With tetrabutyl ammonium fluoride, iodine, trifluoroacetic acid in 1,2-dichloro-ethane, electrolysis Lines, Robert; Parker, Vernon D.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 34; nb. 1; (1980); p. 47 - 52 View in Reaxys With xenon difluoride, iodine in dichloromethane, Time= 1.5h, Ambient temperature Shellhamer, Dale F.; Jones, Brian C.; Pettus, Benjamin J.; Pettus, Tobiah L.; Stringer, Joy Merry; Heasley, Victor L.; Journal of Fluorine Chemistry; vol. 88; nb. 1; (1998); p. 37 - 39 View in Reaxys With dipotassium peroxodisulfate, iodine in dichloromethane, trifluoroacetic acid, Time= 69h, T= 36 - 38 °C Hossain, Md. Delwar; Oyamada, Juzo; Kitamura, Tsugio; Synthesis; nb. 5; (2008); p. 690 - 692 View in Reaxys With iodine, mercury(II) oxide in dichloromethane Liang, Zhidan; Hou, Weizhe; Du, Yunfei; Zhang, Yongliang; Pan, Yan; Mao, Deng; Zhao, Kang; Organic Letters; vol. 11; nb. 21; (2009); p. 4978 - 4981 View in Reaxys With cerium(IV) oxide, dihydrogen peroxide, iodine in water, pH= 1.5, Reflux Zhang, Peng; Sun, Dongqing; Wen, Mingwei; Yang, Jingkui; Zhou, Kebin; Wang, Zhixiang; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 720 - 729 View in Reaxys With N-Bromosuccinimide, acetic acid in 1,2-dichloro-ethane, Time= 0.5h, T= 80 °C , Temperature Losch; Kolb; Astafan; Daou; Pinard; Pale; Louis; Green Chemistry; vol. 18; nb. 17; (2016); p. 4714 - 4724 View in Reaxys

Rx-ID: 1711211 View in Reaxys 4/1037 Yield

Conditions & References With copper(l) iodide, potassium iodide, Time= 5h, T= 200 °C , Inert atmosphere, Finkelstein reaction Yamashita, Ken-Ichi; Tsuboi, Michihiro; Asano, Motoko S.; Sugiura, Ken-Ichi; Synthetic Communications; vol. 42; nb. 2; (2012); p. 170 - 175 View in Reaxys With aluminum oxide, copper(l) iodide in neat (no solvent), Time= 27h, T= 150 °C , different substrates, reagents, solvents and reaction times and temperature, Product distribution Clark, James H.; Jones, Craig W.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1987); p. 1409 - 1410 View in Reaxys With aluminum oxide, copper(l) iodide in neat (no solvent), Time= 27h, T= 150 °C

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Clark, James H.; Jones, Craig W.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1987); p. 1409 - 1410 View in Reaxys 1; 4 : Preparation of Iodobenzene Example 1 Preparation of Iodobenzene 15.7 g (0.1 mole) of bromobenzene is dissolved in 150 mL of n-pentanol. 2 equivalents of sodium iodide and 10 mole percent of 1,3-propanediamine are added to the bromobenzene solution. The reaction mixture is refluxed at 130° C. for eighteen (18) hours to produce iodobenzene, as shown in reaction scheme (4). [Insert Chemical Drawing (4)] The reaction proceeds very rapidly. The reaction mixture is cooled to 80° C. and washed with a 30percent ammonium hydroxide solution. The organic phase is washed with deionized water and brine. The organic phase is then dried over anhydrous sodium sulfate. The dried organic phase is subjected to rotary evaporation and/or vacuum distillation to afford a 92percent yield of high purity iodobenzene. With Trimethylenediamine, sodium iodide, copper(l) iodide in pentan-1-ol, Time= 18h, T= 130 °C , Heating / reflux Patent; XEROX CORPORATION; US2005/234272; (2005); (A1) English View in Reaxys 2.2. General procedure for aryl and heteroaryl bromide–iodideexchange reaction General procedure: A Schlenk tube was charged with Cu2O (7.2 mg, 10 molpercent), l-proline (11.5 mg, 20 molpercent), aryl (or heteroaryl) bromide (1 or 3,0.50 mmol), potassium iodide (KI) (249 mg, 0.75 mmol), and EtOH(1.5 mL) under nitrogen atmosphere. The Schlenk tube was sealedwith a teflon valve, and then the reaction mixture was stirred at110C for a period (the reaction progress was monitored by GCanalysis). After the reaction was completed, GC yield of high volatileproduct was determined using an appropriate internal standard(chlorobenzene or 1-chloro-4-methylbenzene) or the solvent wasremoved under reduced pressure. The residue obtained was puri-fied via silica gel chromatography (eluent: petroleum ether/ethylacetate = 10/1) to afford aryl iodides 2a–2o or heteroaryl iodides4a–4g. With copper(I) oxide, L-proline, potassium iodide in ethanol, Time= 30h, T= 110 °C , Schlenk technique, Inert atmosphere, Sealed tube Feng, Xiujuan; Li, Lingyu; Yu, Xiaoqiang; Yamamoto, Yoshinori; Bao, Ming; Catalysis Today; vol. 274; (2016); p. 129 132 View in Reaxys With potassium iodide, methoxybenzene, nickel dibromide in various solvent(s), Time= 1h, T= 90 °C , electrolysis; variation of catalyst, temperature, KI concentration, time; other reagent NBu4I, educts: aromatic or vinylic bromides, Product distribution Meyer, Gilbert; Rollin, Yolande; Perichon, Jacques; Tetrahedron Letters; vol. 27; nb. 30; (1986); p. 3497 - 3500 View in Reaxys With copper(l) iodide in N,N-dimethyl acetamide, T= 137 °C , equilibrium order; also at 53 deg C, Equilibrium constant Couture, Christiane; Paine, Anthony James; Canadian Journal of Chemistry; vol. 63; (1985); p. 111 - 120 View in Reaxys With KI-CuI-alumina in various solvent(s), Time= 18h, T= 150 °C , other reagents, Product distribution Clark, James H.; Jones, Craig W.; Duke, Catherine V. A.; Miller, Jack M.; Journal of Chemical Research, Miniprint; nb. 8; (1989); p. 1745 - 1758 View in Reaxys With tetra-(n-butyl)ammonium iodide, o-CH3C6H4NiBr(PEt3)2 in benzene, Time= 20h, T= 80 °C , sealed tube, Yield given Tsou, T. T.; Kochi, J. K.; Journal of Organic Chemistry; vol. 45; nb. 10; (1980); p. 1930 - 1937 View in Reaxys With methoxybenzene, nickel dibromide in various solvent(s), Time= 1h, T= 90 °C , electrolysis, Yield given Meyer, Gilbert; Rollin, Yolande; Perichon, Jacques; Tetrahedron Letters; vol. 27; nb. 30; (1986); p. 3497 - 3500 View in Reaxys With iodine, lithium

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Nakamura, Eiichi; Aoki, Satoshi; Sekiya, Kouichi; Oshino, Hiroji; Kuwajima, Isao; Journal of the American Chemical Society; vol. 109; nb. 26; (1987); p. 8056 - 8066 View in Reaxys With KI-CuI-alumina in various solvent(s), Time= 18h, T= 150 °C Clark, James H.; Jones, Craig W.; Duke, Catherine V. A.; Miller, Jack M.; Journal of Chemical Research, Miniprint; nb. 8; (1989); p. 1745 - 1758 View in Reaxys With caesium carbonate, potassium iodide, copper(l) iodide in toluene, Time= 12h, T= 110 °C Rao, Honghua; Jin, Ying; Fu, Hua; Jiang, Yuyang; Zhao, Yufen; Chemistry - A European Journal; vol. 12; nb. 13; (2006); p. 3636 - 3646 View in Reaxys Stage 1: With indium, bathophenanthroline, 3-chloroprop-1-ene, lithium chloride, cobalt(II) bromide in tetrahydrofuran, Time= 23h, T= 100 °C , Inert atmosphere Stage 2: With iodine in tetrahydrofuran, Time= 1h, T= 0 - 20 °C , Inert atmosphere Adak, Laksmikanta; Yoshikai, Naohiko; Journal of Organic Chemistry; vol. 76; nb. 18; (2011); p. 7563 - 7568 View in Reaxys With iodine, sodium iodide in acetonitrile, Time= 18h, T= 20 °C , Inert atmosphere, UV-irradiation, Green chemistry, Reagent/ catalyst, Solvent, Wavelength, Concentration Li, Lu; Liu, Wenbo; Zeng, Huiying; Mu, Xiaoyue; Cosa, Gonzalo; Mi, Zetian; Li, Chao-Jun; Journal of the American Chemical Society; vol. 137; nb. 26; (2015); p. 8328 - 8331 View in Reaxys With copper(l) iodide, 3-azapentane-1,5-diamine, sodium iodide in acetonitrile, Time= 24h, T= 110 °C , Inert atmosphere, Finkelstein Reaction Jin, Xiaodong; Davies, Robert P.; Catalysis Science and Technology; vol. 7; nb. 10; (2017); p. 2110 - 2117 View in Reaxys

H 2N

I I

Rx-ID: 8877041 View in Reaxys 5/1037 Yield

Conditions & References With sodium hydrogensulfite, sodium nitrite in ethanol, water, acetic acid, Time= 20h, T= 24 °C Geoffroy, Otto J.; Morinelli, Thomas A.; Meier, G. Patrick; Tetrahedron Letters; vol. 42; nb. 32; (2001); p. 5367 - 5369 View in Reaxys With tetrahydrofuran, tert.-butylnitrite, salicylic acid, Time= 3h, T= 20 °C , Schlenk technique, Inert atmosphere Felipe-Blanco, Diego; Alonso, Francisco; Gonzalez-Gomez, Jose C.; Advanced Synthesis and Catalysis; vol. 359; nb. 16; (2017); p. 2857 - 2863 View in Reaxys

I I

NH 2

Rx-ID: 40509763 View in Reaxys 6/1037 Yield

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Majek, Michal; Filace, Fabiana; Von Wangelin, Axel Jacobi; Chemistry - A European Journal; vol. 21; nb. 12; (2015); p. 4518 - 4522 View in Reaxys With tetrahydrofuran, tert.-butylnitrite, salicylic acid, Time= 3h, T= 20 °C , Schlenk technique, Inert atmosphere Felipe-Blanco, Diego; Alonso, Francisco; Gonzalez-Gomez, Jose C.; Advanced Synthesis and Catalysis; vol. 359; nb. 16; (2017); p. 2857 - 2863 View in Reaxys

NH 2

Rx-ID: 40509765 View in Reaxys 7/1037 Yield

Conditions & References Stage 1: With tetrafluoroboric acid, acetic acid, isopentyl nitrite in water, Time= 0.0833333h, T= 20 °C Stage 2: With eosin B disodium salt in N,N-dimethyl-formamide, Time= 0.5h, T= 18 °C , Inert atmosphere, Irradiation Majek, Michal; Filace, Fabiana; Von Wangelin, Axel Jacobi; Chemistry - A European Journal; vol. 21; nb. 12; (2015); p. 4518 - 4522 View in Reaxys With tetrahydrofuran, tert.-butylnitrite, salicylic acid, Time= 3h, T= 20 °C , Schlenk technique, Inert atmosphere Felipe-Blanco, Diego; Alonso, Francisco; Gonzalez-Gomez, Jose C.; Advanced Synthesis and Catalysis; vol. 359; nb. 16; (2017); p. 2857 - 2863 View in Reaxys

HO B

Rx-ID: 40683542 View in Reaxys 8/1037 Yield

Conditions & References With C19H23N2OPd(1+) Boeser, Cornelia L.; Holder, Jeffrey C.; Taylor, Buck L. H.; Houk; Stoltz, Brian M.; Zare, Richard N.; Chemical Science; vol. 6; nb. 3; (2015); p. 1917 - 1922 View in Reaxys 7 : Example 7 p-Iodoboric acid (1 mmol),Potassium methoxide (0.05 mmol), 2 mL of methanol or ethanol were successively added into a 10 mL sealed tube, heated and stirred in a 120 ° C. oil bath for 12 hours,The reaction was completed and the exact yield of the product was determined by GC by adding an equivalent of mesitylene to the crude product as an internal standard.According to GC, when using methanol or ethanol as the reaction solvent, the yields were 77percent and 70percent, respectively. With potassium methanolate in methanol, Time= 12h, T= 120 °C , Sealed tube, Green chemistry, Catalytic behavior, Solvent Patent; Taizhou University; Yao Wubing; (7 pag.); CN107188773; (2017); (A) Chinese View in Reaxys

O S

Rx-ID: 45665365 View in Reaxys 9/1037 Yield

Conditions & References With iodine, lithium fluoride, sodium iodide in acetonitrile, Time= 48h, Inert atmosphere, UV-irradiation, Schlenk technique Liu, Wenbo; Yang, Xiaobo; Gao, Yang; Li, Chao-Jun; Journal of the American Chemical Society; vol. 139; nb. 25; (2017); p. 8621 - 8627

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View in Reaxys

F O

I S O

F O

Rx-ID: 45665384 View in Reaxys 10/1037 Yield

Conditions & References With iodine, lithium fluoride, sodium iodide in acetonitrile, Time= 24h, T= 25 °C , Inert atmosphere, UV-irradiation, Schlenk technique Liu, Wenbo; Yang, Xiaobo; Gao, Yang; Li, Chao-Jun; Journal of the American Chemical Society; vol. 139; nb. 25; (2017); p. 8621 - 8627 View in Reaxys

Rx-ID: 46879516 View in Reaxys 11/1037 Yield

Conditions & References 4 : Reaction of 1, 4-diiodobenzene with 1,3-di-tert-butyl-imidazolidine to provide iodobenzene Reaction of 1, 4-diiodobenzene with 1,3-di-tert-butyl-imidazolidine to provide iodobenzene In a 100 mL Schlenk flask, 1,3-di-tert-butyl-imidazolidine (0.16 g, 0.87 mmol) was dissolved in 5 mL of 1,4-dioxane. A solution of 1,4-diiodobenzene (0.15 g, 0.45 mmol) in 3 mL of 1,4-dioxane was added with stirring. After 30 minutes of heating at 100° C. a fine white solid formed. The precipitate continued to collect after heating for 1 day. The final off-white product was washed with ether. Yield 0.07 g, 26percent. 1H-NMR and 13C-NMR of the precipitate showed formation of the imidazolidinium iodide salt. 1HNMR (400 MHz, CDCl3): δ 1.56 [s, 18H, C(CH3)3], 4.09 [s, 4H, NCH2], 8.13 [s, 1H, N2CH+]. 13C-NMR

(400 MHz, CDCl3): δ 28.2 [C(CH3)3], 45.5 [NCH2], 57.2 [C(CH2)2], 152.2 [CH+]. GC-MS of the supernatant showed

conversion of 1,4-diiodobenzene to iodobenzene. EI-MS (pos. ions, 70 eV) m/z (rel. int.)=204 (100) [M]+, 127 (7.8), 77 (69), 51 (22). With 1,3-bis(1,1-dimethylethyl)imidazolidin-2-ylidene in 1,4-dioxane, Time= 24h, T= 100 °C Patent; UNIVERSITY OF GUELPH; Denk, Michael K.; Milutinovic, Nicholas; Marczenko, Katherine; (14 pag.); US9744392; (2017); (B1) English View in Reaxys

H 2N

Rx-ID: 712773 View in Reaxys 12/1037 Yield

Conditions & References Stage 1: With hydrogenchloride, sodium nitrite in water, toluene, Time= 0.0333333h, T= 25 °C Stage 2: With sodium iodide in water, toluene, Time= 2.5h, T= 25 °C , Reagent/catalyst Yang, Hengquan; Fu, Luman; Wei, Lijuan; Liang, Jifen; Binks, Bernard P.; Journal of the American Chemical Society; vol. 137; nb. 3; (2015); p. 1362 - 1371 View in Reaxys With 1,1,1,2,2,2-hexamethyldisilane, N-benzyl-N,N,N-triethylammonium chloride, iodine, sodium nitrite in tetrachloromethane, 1.) 0 deg C, 1.5 h, 2.) r.t., 12 h Lee, Jong Gun; Cha, Hee Tae; Tetrahedron Letters; vol. 33; nb. 22; (1992); p. 3167 - 3168 View in Reaxys Stage 1: With nicotinic acid sulfate, sodium nitrite in water, Time= 0.333333h, T= 20 °C , Grinding Stage 2: With sodium iodide in water, T= 20 °C

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Hajipour, Abdol Reza; Seddighi, Mohadeseh; Organic Preparations and Procedures International; vol. 43; nb. 3; (2011); p. 292 - 296 View in Reaxys Stage 1: With sulfuric acid, silica gel, sodium nitrite, T= 20 °C , grinding, Neat (no solvent) Stage 2: With water, T= 20 °C , grinding, Neat (no solvent) Stage 3: With potassium iodide, Time= 0.166667h, T= 20 °C , grinding, Neat (no solvent), Sandmeyer reaction Zarei, Amin; Hajipour, Abdol R.; Khazdoozd, Leila; Synthesis; nb. 6; (2009); p. 941 - 944; Art.No: Z19108SS View in Reaxys Stage 1: With sodium nitrite in neat (no solvent), Time= 0.1h, T= 0 °C , Green chemistry Stage 2: With sodium iodide in neat (no solvent), Time= 0.1h, T= 0 - 20 °C , Green chemistry Isaad, Jalal; RSC Advances; vol. 4; nb. 90; (2014); p. 49333 - 49341 View in Reaxys With diiodomethane, isopentyl nitrite, 1.) room temperature, 0.5 h, 2.) 80 deg C, 2 h Smith,William B.; Ho, Oliver Chenpu; Journal of Organic Chemistry; vol. 55; nb. 8; (1990); p. 2543 - 2545 View in Reaxys Diazotization–iodination of aromatic amines General procedure: An aromaticamine (1 mmol), nanomagnetic-supported sulfonic acid (c-Fe2O3–SO3H)(0.65 g), NaNO2 (2 mmol, 0.138 g), and 0.2 mL of H2O were homogenized bygrinding in a mortar with a pestle for a few minutes. Formation of a reddishbrowngas was observed as soon as H2O was added. The diazotization reactionlasted for approximately 5–30 min. Next, KI (2.5 mmol, 0.415 g) was added tothe diazonium salt and grinding was continued for 10–20 min. After completionof the reaction, the mixture was triturated with EtOAc (5 mL). The c-Fe2O3–SO3K was separated from the solution using a magnetic bar. The organic layerwas treated with aq 10percent Na2SO3 (15 mL), then dried over anhydrous Na2SO4.After evaporation of the solvent, the crude product was afforded. Purifiedproducts were obtained by recrystallization from ethanol or by flashchromatography (n-hexane–EtOAc, 95:5). Stage 1: With water, sodium nitrite in neat (no solvent), T= 20 °C Stage 2: With potassium iodide in neat (no solvent), T= 20 °C Kolvari, Eskandar; Amoozadeh, Ali; Koukabi, Nadiya; Otokesh, Somayeh; Isari, Mohsen; Tetrahedron Letters; vol. 55; nb. 27; (2014); p. 3648 - 3651 View in Reaxys With hydrogen iodide, potassium iodide, sodium nitrite, multistep reaction; diazotization and Sandmeyer reaction in polyethylene glycol-CH2Cl2; 0 deg C to r.t. Suzuki, Nobutaka; Kaneko, Yoshihiro; Nomoto, Tateo; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 22; (1984); p. 1523 - 1524 View in Reaxys Diazotization.Behandlung der Diazoniumsalz-Loesung mit KI Lucas; Kennedy; Organic Syntheses; vol. Coll. Vol. II; (1943); p. 351 View in Reaxys With potassium iodide, Reaktion ueber mehrere Stufen Sandmeyer; Chemische Berichte; vol. 17; (1884); p. 1634 View in Reaxys Gattermann; View in Reaxys With hydrogen iodide, potassium iodide, sodium nitrite, 1.) water, poly(ethylene glycol), CH2Cl2, 0 deg C; 2.) poly(ethylene glycol), CH2Cl2, from 0 deg C to RT, Yield given. Multistep reaction Suzuki, Nobutaka; Azuma, Terukazu; Kaneko, Yoshihiro; Izawa, Yasuji; Tomioka, Hideo; Nomoto, Tateo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 645 - 648 View in Reaxys

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With sulfuric acid, potassium iodide, sodium nitrite, 1.) from 0 deg C to 5 deg C, 0.75 h, 2.) water, 5 deg C, 1 h, Multistep reaction Stillings, Michael R.; Welbourn, Anthony P.; Walter, Donald S.; Journal of Medicinal Chemistry; vol. 29; nb. 11; (1986); p. 2280 - 2284 View in Reaxys Reaction Steps: 2 1: 67 percent / isoamyl nitrite / ethanol; H2O / Ambient temperature 2: sodium iodide, trimethylsilyl chloride / acetonitrile / 0.25 h / 60 °C With chloro-trimethyl-silane, sodium iodide, isopentyl nitrite in ethanol, water, acetonitrile Smith,William B.; Ho, Oliver Chenpu; Journal of Organic Chemistry; vol. 55; nb. 8; (1990); p. 2543 - 2545 View in Reaxys Stage 1: With silica-gel-supported sulfuric acid, sodium nitrite, Milling Stage 2: With potassium iodide in water, Milling Hajipour, Abdol Reza; Azizi, Ghobad; Green Chemistry; vol. 15; nb. 4; (2013); p. 1030 - 1034 View in Reaxys Stage 1: With sulfuric acid, acetic acid, sodium nitrite in water, Time= 1h, T= 0 °C Stage 2: With potassium iodide in water, T= 20 °C Shao, Changdong; Shi, Guangfa; Zhang, Yanghui; European Journal of Organic Chemistry; vol. 2016; nb. 33; (2016); p. 5529 - 5538 View in Reaxys -1 F (v4)

B FF

I I+

Rx-ID: 2243660 View in Reaxys 13/1037 Yield

Conditions & References With Johnson & Matthey type 440 in 1,2-dimethoxyethane, Time= 2h, T= 100 °C Collins, Karl D.; Honeker, Roman; Vásquez-Céspedes, Suhelen; Tang, Dan-Tam D.; Glorius, Frank; Chemical Science; vol. 6; nb. 3; (2015); p. 1816 - 1824 View in Reaxys

40 %

With palladium diacetate, Time= 0.166667h, T= 50 °C , Microwave irradiation Arun; Reddy, P. O. Venkataramana; Pilania, Meenakshi; Kumar, Dalip; European Journal of Organic Chemistry; vol. 2016; nb. 12; (2016); p. 2096 - 2100 View in Reaxys With copper in acetonitrile, T= 20 °C , Ea, ΔS, Rate constant, Thermodynamic data, Kinetics Ptitsyna, O. A.; Kim, T. L.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 10; (1981); p. 1966 - 1967; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1981); p. 2386 - 2388 View in Reaxys

HO B

Rx-ID: 4855088 View in Reaxys 14/1037 Yield

Conditions & References With copper(I) oxide, ammonium hydroxide, oxygen, potassium iodide in water, Time= 24h, T= 25 °C

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Yang, Haijun; Li, Yong; Jiang, Min; Wang, Junmei; Fu, Hua; Chemistry - A European Journal; vol. 17; nb. 20; (2011); p. 5652 - 5660 View in Reaxys General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v With iodine, potassium carbonate in acetonitrile, Time= 10h, T= 80 °C , Inert atmosphere, Schlenk technique, Sealed tube Niu, Liting; Zhang, Hao; Yang, Haijun; Fu, Hua; Synlett; vol. 25; nb. 7; (2014); p. 995 - 1000; Art.No: 691 View in Reaxys 2.2 General experimental procedure for iodo-deboronation of arylboronic acids General procedure: 0.05 mmol Cu(NO3)2·3H2O, 1 mmol I2, 1 mmol arylboronic acids and 0.8 mL acetonitrile were added into an about 15 mL tube. Subsequently, the reaction tube was sealed to perform the reaction for 6 h without inert gas protection. Once the reaction time was reached, 10 mL water was added. The mixture was then extracted with dichloromethane (3 x 15 mL). The combined organic layers were washed with aqueous sodium hyposulfite, distilled water, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data. With copper(II) nitrate trihydrate, iodine in acetonitrile, Time= 6h, T= 20 °C , Sealed tube, Reagent/catalyst, Solvent, Concentration Ren, Yun-Lai; Tian, Xin-Zhe; Dong, Chuanhua; Zhao, Shuang; Wang, Jianji; Yan, Mengjie; Qi, Xiaoguang; Liu, Guihua; Catalysis Communications; vol. 32; (2013); p. 15 - 17 View in Reaxys General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product. With 1,10-Phenanthroline, oxygen, potassium iodide, copper(ll) bromide in N,N-dimethyl-formamide, Time= 20h, T= 80 °C Zhang, Guangyou; Lv, Guanglei; Li, Liping; Chen, Fan; Cheng, Jiang; Tetrahedron Letters; vol. 52; nb. 16; (2011); p. 1993 - 1995 View in Reaxys With N-iodo-succinimide in acetonitrile, Time= 14h, T= 81 °C Thiebes, Christoph; Prakash, G. K. Surya; Petasis, Nicos A.; Olah, George A.; Synlett; nb. 2; (1998); p. 141 - 142 View in Reaxys With iodine, palladium diacetate, copper(II) acetate monohydrate, potassium carbonate in 1-methyl-pyrrolidin-2-one, Time= 6h, T= 160 °C , Inert atmosphere Tian, Xinzhe; Sun, Yanpei; Dong, Chuanhua; Zhang, Kaixuan; Liang, Tengfei; Zhang, Yu; Hou, Chaodong; Chemistry Letters; vol. 41; nb. 7; (2012); p. 719 - 721 View in Reaxys Reaction Steps: 2 1: neat (no solvent) / 1 h / 100 °C / Inert atmosphere 2: iodine / tetrahydrofuran / 0.5 h / -15 - 0 °C With iodine in tetrahydrofuran Oikawa, Asuka; Kindaichi, Gan; Shimotori, Yasutaka; Okimoto, Mitsuhiro; Hoshi, Masayuki; Tetrahedron; vol. 71; nb. 11; (2015); p. 1705 - 1711 View in Reaxys With copper(l) iodide, N-iodomorpholine-hydrogen iodide in methanol, Time= 24h, T= 20 °C

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Tale; Toradmal; Gopula; RSC Advances; vol. 5; nb. 103; (2015); p. 84910 - 84919 View in Reaxys 1 : 4.1. Typical procedure for the iodination of 1a-t by (CF3)2CFI General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol,), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were placed in a closed tube with a rubber stopper. The mixture was reacted at room temperature equipped with an air balloon for 24 h. The resulting suspension was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness. The crude product was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate = 20: 1 (v/v) as eluent to give 0.086 g of 2j as a light yellow solid (0.35 mmol, 87percent). With perfluoroisopropyl iodide, copper, hydroquinone in N,N-dimethyl-formamide, Time= 24h, T= 20 °C Liu, Xi-Hai; Leng, Jing; Jia, Su-Jiao; Hao, Jian-Hong; Zhang, Fanglin; Qin, Hua-Li; Zhang, Cheng-Pan; Journal of Fluorine Chemistry; vol. 189; (2016); p. 59 - 67 View in Reaxys

(v3) N (v4) N – 2+ Ni N C –(v5)(v4) (v4)

(v4)

Rx-ID: 42376259 View in Reaxys 15/1037 Yield

Conditions & References With iodine, Time= 0.1h, T= 22 °C , Schlenk technique, Glovebox Xu, Hongwei; Diccianni, Justin B.; Katigbak, Joseph; Hu, Chunhua; Zhang, Yingkai; Diao, Tianning; Journal of the American Chemical Society; vol. 138; nb. 14; (2016); p. 4779 - 4786 View in Reaxys

N (v4)

(v4)

Ni 2+ C– (v4)

N– (v3)

Rx-ID: 42376285 View in Reaxys 16/1037 Yield

Conditions & References Reaction Steps: 2 1: toluene / Schlenk technique; Glovebox 2: iodine / 0.1 h / 22 °C / Schlenk technique; Glovebox With iodine in toluene Xu, Hongwei; Diccianni, Justin B.; Katigbak, Joseph; Hu, Chunhua; Zhang, Yingkai; Diao, Tianning; Journal of the American Chemical Society; vol. 138; nb. 14; (2016); p. 4779 - 4786 View in Reaxys

O O

O I

I O

Rx-ID: 42557259 View in Reaxys 17/1037

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Yield

Conditions & References With iodine in [D3]acetonitrile Achar, Tapas Kumar; Maiti, Saikat; Mal, Prasenjit; Organic and Biomolecular Chemistry; vol. 14; nb. 20; (2016); p. 4654 4663 View in Reaxys

I N

Rx-ID: 43194982 View in Reaxys 18/1037 Yield

Conditions & References

6 %, 30 %

in tetrahydrofuran, diethylene glycol dimethyl ether, Time= 1h, T= 25 - 110 °C Okura, Keisho; Shirakawa, Eiji; European Journal of Organic Chemistry; vol. 2016; nb. 18; (2016); p. 3043 - 3046 View in Reaxys

O–

I+ O

F O

Rx-ID: 44483392 View in Reaxys 19/1037 Yield

Conditions & References

60 %

With copper(l) chloride in 1,4-dioxane, Time= 0.5h, T= 50 °C , Microwave irradiation Arun; Reddy, P. O. Venkataramana; Pilania, Meenakshi; Kumar, Dalip; European Journal of Organic Chemistry; vol. 2016; nb. 12; (2016); p. 2096 - 2100 View in Reaxys

O–

I+ O

F F

Rx-ID: 44483393 View in Reaxys 20/1037 Yield

Conditions & References With copper(l) chloride in 1,4-dioxane, Time= 12h, T= 80 °C , Reagent/catalyst Arun; Reddy, P. O. Venkataramana; Pilania, Meenakshi; Kumar, Dalip; European Journal of Organic Chemistry; vol. 2016; nb. 12; (2016); p. 2096 - 2100 View in Reaxys

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I+

O –O

S O

Rx-ID: 44483417 View in Reaxys 21/1037 Yield

Conditions & References With palladium diacetate, Time= 0.166667h, T= 50 °C , Microwave irradiation Arun; Reddy, P. O. Venkataramana; Pilania, Meenakshi; Kumar, Dalip; European Journal of Organic Chemistry; vol. 2016; nb. 12; (2016); p. 2096 - 2100 View in Reaxys

I+ Br–

Rx-ID: 44483420 View in Reaxys 22/1037 Yield

Rx-ID: 852443 View in Reaxys 23/1037 Yield

Conditions & References 4. 2. Typical Procedure for Iodinationof Alcohol General procedure: To a suspension of polymer-bound triphenylphosphine (1.2 mmol) in anhydrous acetonitrile (10 mL) were added iodine (1 mmol) and 1,6-hexanediol diol (1mmol). The reaction mixture was irradiated in microwave reactor at 120 °C for 3 min. The reaction mixture was filtered over a filter paper and washed with chloroform.The filtrate was extracted with aqueous sodium thiosulfate solution and dried with anhydrous sodium sulfate.The reafter, solvent was removed under reduced pressure to obtain 6-iodohexan-1-ol (30) in 93percent With iodine in acetonitrile, Time= 0.0833333h, T= 120 °C , Microwave irradiation, chemoselective reaction Das, Diparjun; Chanda, Tridib; Rokhum, Lalthazuala; Acta Chimica Slovenica; vol. 62; nb. 4; (2015); p. 775 - 783 View in Reaxys With phosphorus, iodine Scrugham; Justus Liebigs Annalen der Chemie; vol. 92; (1854); p. 318; Journal of the Chemical Society; vol. 7; (1855); p. 243 View in Reaxys

O O I

Rx-ID: 1995034 View in Reaxys 24/1037 Yield

Conditions & References With iodine in chloroform, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

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With iodine in chloroform, Ambient temperature, further regents, further products, Product distribution Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys With hydrogen bromide, Time= 0.333333h, T= 0 °C , Yield given Shabarov, Yu. S.; Pisanova, E. V.; Saginova, L. G.; Journal of Organic Chemistry USSR (English Translation); vol. 17; (1981); p. 1685 - 1689; Zhurnal Organicheskoi Khimii; vol. 17; nb. 9; (1981); p. 1886 - 1892 View in Reaxys Reaction Steps: 3 1: KOH / methanol 2: CF3CO2H 3: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C With potassium hydroxide, boron trifluoride diethyl etherate, trifluoroacetic acid in tetrahydrofuran, methanol Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys Reaction Steps: 3 1: KOH / methanol 2: CF3CO2H 3: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C With potassium hydroxide, boron trifluoride diethyl etherate, trifluoroacetic acid in tetrahydrofuran, methanol Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys Reaction Steps: 3 1: KOH / methanol 2: CF3CO2H 3: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C With potassium hydroxide, boron trifluoride diethyl etherate, trifluoroacetic acid in tetrahydrofuran, methanol Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys With palladium diacetate, potassium carbonate in PEG-400, Time= 24h, T= 40 °C , under air Qu, Xiaoming; Sun, Peng; Li, Tingyi; Mao, Jincheng; Advanced Synthesis and Catalysis; vol. 353; nb. 7; (2011); p. 1061 1066 View in Reaxys Reaction Steps: 2 1: dichloromethane / Glovebox; Inert atmosphere 2: chloroform-d1 in chloroform-d1, dichloromethane Pell, Thomas P.; Couchman, Shannon A.; Ibrahim, Sara; Wilson, David J. D.; Smith, Brian J.; Barnard, Peter J.; Dutton, Jason L.; Inorganic Chemistry; vol. 51; nb. 23; (2012); p. 13034 - 13040 View in Reaxys Reaction Steps: 2 1: acetic acid / water / 0.5 h / 0 °C 2: [D3]acetonitrile / 0.5 h / 0 °C With acetic acid in [D3]acetonitrile, water Tokarz, Paweł; Kaszyński, Piotr; Domagała, Sławomir; Woźniak, Krzysztof; Journal of Organometallic Chemistry; vol. 798; (2015); p. 70 - 79 View in Reaxys Reaction Steps: 3 1: water / acetonitrile / 0.5 h 2: dichloromethane / -78 deg C, then 24 h, room t.

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3: copper(I) triflate / acetonitrile / 6 h / 25 °C With water, copper(I) triflate in dichloromethane, acetonitrile Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys Reaction Steps: 3 1: water / acetonitrile / 0.5 h 2: dichloromethane / 8 h / Ambient temperature 3: copper(I) triflate / acetonitrile / 4 h / 25 °C With water, copper(I) triflate in dichloromethane, acetonitrile Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys Reaction Steps: 3 1: water / acetonitrile / 0.5 h 2: dichloromethane / 96 h / Ambient temperature 3: copper(I) triflate / acetonitrile / 18 h / Heating With water, copper(I) triflate in dichloromethane, acetonitrile Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

Rx-ID: 3377520 View in Reaxys 25/1037 Yield

Conditions & References With copper(l) iodide, pyrographite in neat (no solvent), Time= 60h, T= 130 °C Clark, James H.; Jones, Craig W.; Journal of the Chemical Society, Chemical Communications; nb. 18; (1987); p. 1409 - 1410 View in Reaxys Reaction Steps: 2 1: Na / petroleum ether With Na in petroleum ether vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys With iodine, sodium iodide in acetonitrile, Time= 18h, T= 20 °C , Inert atmosphere, UV-irradiation, Green chemistry Li, Lu; Liu, Wenbo; Zeng, Huiying; Mu, Xiaoyue; Cosa, Gonzalo; Mi, Zetian; Li, Chao-Jun; Journal of the American Chemical Society; vol. 137; nb. 26; (2015); p. 8328 - 8331 View in Reaxys

I Sn

Rx-ID: 39533926 View in Reaxys 26/1037 Yield

Conditions & References General procedure for iododestannylation of phenyl-tributylstannane with iodine General procedure: Into a 25 mL round-bottomed ask was added phenylboronicacid (0.122 g, 1 mmol), and the ask was purged with argon. Either solvent (3 mL) and tributyltin methoxide (0.321 g, 1 mmol) or tributyltin methoxide (0.321 g, 1 mmol) alone was then added at room temperature and the mixture was stirred at different reaction temperatures and times. The reaction mix-

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ture was cooled to15 C, and a solution of I2 (0.279 g, 1.1 mmol) in THF (1 mL) was added dropwise. The resulting mixture was allowed to warm to 0 C, stirred for 0.5 h, and treated with aqueous Na2O3S2 to remove excess I2. The organic phase was analyzed by GC. With iodine in tetrahydrofuran, Time= 0.5h, T= -15 - 0 °C Oikawa, Asuka; Kindaichi, Gan; Shimotori, Yasutaka; Okimoto, Mitsuhiro; Hoshi, Masayuki; Tetrahedron; vol. 71; nb. 11; (2015); p. 1705 - 1711 View in Reaxys O

I 2

O 2H 2H

Rx-ID: 39631382 View in Reaxys 27/1037 Yield

Conditions & References With pyridine, tetradeuterioacetic acid, palladium diacetate, T= 100 °C , Reagent/catalyst Cook, Amanda K.; Sanford, Melanie S.; Journal of the American Chemical Society; vol. 137; nb. 8; (2015); p. 3109 - 3118 View in Reaxys

Rx-ID: 40322330 View in Reaxys 28/1037 Yield

Conditions & References

6 %Chromat.

With iodine, sodium iodide in tetrahydrofuran, Time= 18h, T= 20 °C , Inert atmosphere, UV-irradiation, Green chemistry Li, Lu; Liu, Wenbo; Zeng, Huiying; Mu, Xiaoyue; Cosa, Gonzalo; Mi, Zetian; Li, Chao-Jun; Journal of the American Chemical Society; vol. 137; nb. 26; (2015); p. 8328 - 8331 View in Reaxys

14 %Chromat.

With iodine, sodium iodide in acetonitrile, Time= 18h, T= 20 °C , Inert atmosphere, UV-irradiation, Green chemistry, Solvent Li, Lu; Liu, Wenbo; Zeng, Huiying; Mu, Xiaoyue; Cosa, Gonzalo; Mi, Zetian; Li, Chao-Jun; Journal of the American Chemical Society; vol. 137; nb. 26; (2015); p. 8328 - 8331 View in Reaxys

I+

O–

O N

Rx-ID: 40997175 View in Reaxys 29/1037 Yield

Conditions & References in water, UV-irradiation Feng, Wei; Zhou, Wanfu; Zhang, Shidong; Fan, Yujiao; Yasin, Akram; Yang, Haiyang; RSC Advances; vol. 5; nb. 100; (2015); p. 81784 - 81789 View in Reaxys

2H 2H

I+ B– (v6) HH H BB BBH B H

2 2H 2 H H (v6)

(v6)

(v6) (v6) (v6)(v6)

(v6)(v6) (v6) (v6)

N+

HHB B (v6)

(v6) (v6)(v6)

N+ B– (v6) BHBH BH

(v6)(v6) (v6) (v6)

BB BH BH HB HH (v6) B– H (v6)

Rx-ID: 41720326 View in Reaxys 30/1037

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Yield

Conditions & References 5.8 Kinetic measurements General procedure: The decomposition of iodonium zwitterions 1[NEt4] in CD3CN at 0°C was monitored by 1H NMR. The solvent was cooled to about−25°C, small amount of dimethyl terephthalate as the reference was added followed by about 3mg of the zwitterion. The spectrometer was thermostated prior to introduction of the NMR tube. The ratio of the intensity of the most downfield (7.80ppm, for 1a[NEt4]) or upfield (7.66ppm, 1b[NEt4]) signals of the aromatic protons and reference (8.06ppm) was calculated. A plot of log of the ratio vrs time (30min for 1a[NEt4], and 50min for 1b[NEt4]) gave the decomposition rate. The major organic product of decomposition of [closo-B12H11-1-IPh]− [NEt4]+ (1a[NEt4]) was identified as iodobenzene: 1H NMR (500MHz, CD3CN) δ 7.15 (t, J=7.7 Hz, 2H), 7.38 (tt, J1=7.5Hz, J2=1.1Hz, 1H), 7.73 (dd, J1=8.6Hz, J2=1.1Hz, 2H). Other signals include δ 6.90–7.01 (m), 7.28–7.32 (m), 7.45–7.60 (br m). in [D3]acetonitrile, Time= 0.5h, T= 0 °C , Kinetics Tokarz, Paweł; Kaszyński, Piotr; Domagała, Sławomir; Woźniak, Krzysztof; Journal of Organometallic Chemistry; vol. 798; (2015); p. 70 - 79 View in Reaxys

O O F

O F

F F

Rx-ID: 41842310 View in Reaxys 31/1037 Yield

Conditions & References With cesium fluoride in acetonitrile, Time= 6h, T= 20 °C , Reagent/catalyst, Solvent Zhu, Hui; Zhang, Shusheng; Wang, Haoyang; Xu, Bin; Guo, Yinlong; Chinese Journal of Chemistry; vol. 33; nb. 12; (2015); p. 1365 - 1370 View in Reaxys

Rx-ID: 285927 View in Reaxys 32/1037 Yield

Conditions & References With C32H36Ru in dichloromethane, Time= 1h, T= 20 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst, Solvent So, Shiu-Chun; Cheung, Wai-Man; Wang, Guo-Cang; Kwan Huang, Enrique; Lau, Man-Kit; Zhang, Qian-Feng; Sung, Herman H.-Y.; Williams, Ian D.; Leung, Wa-Hung; Organometallics; vol. 33; nb. 17; (2014); p. 4497 - 4502 View in Reaxys T= 90 - 100 °C Askenasy; Meyer,V.; Chemische Berichte; vol. 26; (1893); p. 1356 View in Reaxys Willgerodt; Chemische Berichte; vol. 25; (1892); p. 3495; Chemische Berichte; vol. 26; (1893); p. 357,1807 View in Reaxys

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Reaction Steps: 2 1: 80 percent / boron trifluoride-diethyl ether / CH2Cl2 / 0.25 h / 0 °C 2: 62 percent / diethyl ether / 3 h / -78 °C With boron trifluoride diethyl etherate in diethyl ether, dichloromethane Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys Reaction Steps: 2 1: 80 percent / boron trifluoride-diethyl ether / CH2Cl2 / 0.25 h / 0 °C 2: 79 percent / tetrahydrofuran / 4 h / -78 °C With boron trifluoride diethyl etherate in tetrahydrofuran, dichloromethane Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys Reaction Steps: 2 1: 80 percent / boron trifluoride-diethyl ether / CH2Cl2 / 0.25 h / 0 °C 2: 40 percent Chromat. / butyllithium / tetrahydrofuran; hexane / 3 h / -78 °C With n-butyllithium, boron trifluoride diethyl etherate in tetrahydrofuran, hexane, dichloromethane Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys Reaction Steps: 2 1: 67 percent / boron trifluoride-diethyl ether / CH2Cl2 / 1.5 h / 0 °C 2: 62 percent / diethyl ether / 3 h / -78 °C With boron trifluoride diethyl etherate in diethyl ether, dichloromethane Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys Reaction Steps: 2 1: 67 percent / boron trifluoride-diethyl ether / CH2Cl2 / 1.5 h / 0 °C 2: 79 percent / tetrahydrofuran / 4 h / -78 °C With boron trifluoride diethyl etherate in tetrahydrofuran, dichloromethane Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys Reaction Steps: 2 1: 67 percent / boron trifluoride-diethyl ether / CH2Cl2 / 1.5 h / 0 °C 2: 40 percent Chromat. / butyllithium / tetrahydrofuran; hexane / 3 h / -78 °C With n-butyllithium, boron trifluoride diethyl etherate in tetrahydrofuran, hexane, dichloromethane Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys Reaction Steps: 3 1.1: dichloromethane 2.1: 18-crown-6 ether / acetone / 2 h / -30 - 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: dichloromethane-d2 / -78 - 20 °C / Inert atmosphere With 18-crown-6 ether in dichloromethane, dichloromethane-d2, acetone Miyamoto, Kazunori; Suzuki, Mai; Suefuji, Takashi; Ochiai, Masahito; European Journal of Organic Chemistry; nb. 18; (2013); p. 3662 - 3666

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View in Reaxys H O

Rx-ID: 37172532 View in Reaxys 33/1037 Yield 27 %, 35 %

Conditions & References With 10% palladium on activated charcoal, 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 12h Yu, Bo; Zhao, Yanfei; Zhang, Hongye; Xu, Jilei; Hao, Leiduan; Gao, Xiang; Liu, Zhimin; Chemical Communications; vol. 50; nb. 18; (2014); p. 2330 - 2333 View in Reaxys F F F O

O O

O N H

F F

O N O

Rx-ID: 37480231 View in Reaxys 34/1037 Yield

Conditions & References in acetonitrile, T= 20 °C Glover, Stephen A.; Rosser, Adam A.; Taherpour, Avat; Greatrex, Ben W.; Australian Journal of Chemistry; vol. 67; nb. 3; (2014); p. 507 - 520 View in Reaxys F F F O

H N

O O

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O N N O

O N O O

Rx-ID: 37480247 View in Reaxys 35/1037 Yield

Conditions & References in acetonitrile Glover, Stephen A.; Rosser, Adam A.; Taherpour, Avat; Greatrex, Ben W.; Australian Journal of Chemistry; vol. 67; nb. 3; (2014); p. 507 - 520 View in Reaxys

O–

I+ O

S F O

2H 2H

Rx-ID: 38169946 View in Reaxys 36/1037 Yield Ca. 15 %Spectr.

Conditions & References Stage 1: With copper(I) thiophene-2-carboxylate in dichloromethane, Time= 13h, T= 70 °C , Sealed tube, Inert atmosphere, Molecular sieve Stage 2: With DOTf in dichloromethane, Time= 6h, T= 20 °C , Sealed tube, Inert atmosphere, Molecular sieve, Overall yield = 53 mg Zhang, Fengzhi; Das, Shoubhik; Walkinshaw, Andrew J.; Casitas, Alicia; Taylor, Michael; Suero, Marcos G.; Gaunt, Matthew J.; Journal of the American Chemical Society; vol. 136; nb. 25; (2014); p. 8851 - 8854 View in Reaxys

O–

I+ O

F F

Rx-ID: 38169947 View in Reaxys 37/1037 Yield

Conditions & References Stage 1: With copper(I) thiophene-2-carboxylate in dichloromethane, Time= 14h, T= 70 °C , Molecular sieve, Inert atmosphere, Sealed tube Stage 2: With trifluorormethanesulfonic acid in dichloromethane, Time= 6h, T= 20 °C , Molecular sieve, Inert atmosphere, Sealed tube, Overall yield = 52 percent; Overall yield = 53 mg Zhang, Fengzhi; Das, Shoubhik; Walkinshaw, Andrew J.; Casitas, Alicia; Taylor, Michael; Suero, Marcos G.; Gaunt, Matthew J.; Journal of the American Chemical Society; vol. 136; nb. 25; (2014); p. 8851 - 8854 View in Reaxys

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I F

I (v1)

NH 2

Rx-ID: 38493885 View in Reaxys 38/1037 Yield

Conditions & References Stage 1: With hydrogen fluoride, sodium nitrite in water, acetonitrile, T= 0 °C , Inert atmosphere Stage 2: in water, N,N-dimethyl-formamide, acetonitrile, Time= 0.25h, T= 0 °C , Inert atmosphere, Overall yield = 47 percentSpectr. Lishchynskyi, Anton; Berthon, Guillaume; Grushin, Vladimir V.; Chemical Communications; vol. 50; nb. 71; (2014); p. 10237 - 10240 View in Reaxys I

H 2N

(v1)

Rx-ID: 38493904 View in Reaxys 39/1037 Yield

Conditions & References Stage 1: With hydrogen fluoride, sodium nitrite in water, acetonitrile, T= 0 °C , Inert atmosphere Stage 2: in water, N,N-dimethyl-formamide, acetonitrile, Time= 0.25h, T= 0 °C , Inert atmosphere, Overall yield = 58 percentSpectr. Lishchynskyi, Anton; Berthon, Guillaume; Grushin, Vladimir V.; Chemical Communications; vol. 50; nb. 71; (2014); p. 10237 - 10240 View in Reaxys

Rx-ID: 32031312 View in Reaxys 40/1037 Yield

Conditions & References

20 %, 16 %

Time= 50h, UV-irradiation Vlasova; Belousova; Vlasov; Vakul'Skaya; Khutsishvili; Voronkov; Doklady Chemistry; vol. 438; nb. 2; (2011); p. 164 - 166 View in Reaxys

20 %, 16 %

Time= 50h, UV-irradiation Voronkov; Vlasova; Belousova; Vlasov; Vakul'Skaya; Prozorova; Khutsishvili; Russian Journal of Organic Chemistry; vol. 49; nb. 1; (2013); p. 17 - 21; Zh. Org. Khim.; vol. 49; nb. 1; (2013); p. 27 - 31,5 View in Reaxys

I O

Rx-ID: 32031314 View in Reaxys 41/1037 Yield 25 %, 14 %

Conditions & References Time= 29h, UV-irradiation Vlasova; Belousova; Vlasov; Vakul'Skaya; Khutsishvili; Voronkov; Doklady Chemistry; vol. 438; nb. 2; (2011); p. 164 - 166 View in Reaxys

25 %, 14 %

Time= 29h, UV-irradiation Voronkov; Vlasova; Belousova; Vlasov; Vakul'Skaya; Prozorova; Khutsishvili; Russian Journal of Organic Chemistry; vol. 49; nb. 1; (2013); p. 17 - 21; Zh. Org. Khim.; vol. 49; nb. 1; (2013); p. 27 - 31,5 View in Reaxys

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N – Sn4+ N– (v3) H – (v5)(v3) N (v4) N

F F

F (v4) C–

F F

(v4)

F F

F (v1) –

F F

N – Sn4+N – (v3) H – (v5)(v3) N (v4)

F F

(v4)

Rx-ID: 34952622 View in Reaxys 42/1037 Yield

Conditions & References

100 %Spectr.

Time= 48h, T= 25 °C Tsay, Olga G.; Kim, Byung-Kwon; Luu, Tuong Loan; Kwak, Juhyoun; Churchill, David G.; Inorganic Chemistry; vol. 52; nb. 4; (2013); p. 1991 - 1999 View in Reaxys

-1 P+

F F

B (v4)

O–

F (v2)

–

-1 F (v4)

B FF

P+ F

P P+

Rx-ID: 34971719 View in Reaxys 43/1037 Yield

Conditions & References Time= 0.333333h, Photolysis, Kinetics Nekipelova, Tatiana D.; Kuzmin, Vladimir A.; Matveeva, Elena D.; Gleiter, Rolf; Zefirov, Nikolay S.; Journal of Physical Organic Chemistry; vol. 26; nb. 2; (2013); p. 137 - 143 View in Reaxys OH

HO B HO

I B

Rx-ID: 35071420 View in Reaxys 44/1037 Yield

Conditions & References With copper(II) nitrate trihydrate, iodine, N,N`-dimethylethylenediamine in N,N-dimethyl-formamide, Time= 6h, T= 20 °C Ren, Yun-Lai; Tian, Xin-Zhe; Dong, Chuanhua; Zhao, Shuang; Wang, Jianji; Yan, Mengjie; Qi, Xiaoguang; Liu, Guihua; Catalysis Communications; vol. 32; (2013); p. 15 - 17 View in Reaxys

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O O

I O

Rx-ID: 35686513 View in Reaxys 45/1037 Yield

Conditions & References With n-butyllithium in dichloromethane-d2, Time= 0.5h, T= -78 °C , Inert atmosphere Miyamoto, Kazunori; Suzuki, Mai; Suefuji, Takashi; Ochiai, Masahito; European Journal of Organic Chemistry; nb. 18; (2013); p. 3662 - 3666 View in Reaxys

O O O

O O–

O O

Li+

I Br

O O

Rx-ID: 35686523 View in Reaxys 46/1037 Yield

Conditions & References in dichloromethane-d2, T= -78 - 20 °C , Inert atmosphere Miyamoto, Kazunori; Suzuki, Mai; Suefuji, Takashi; Ochiai, Masahito; European Journal of Organic Chemistry; nb. 18; (2013); p. 3662 - 3666 View in Reaxys N

O S

O F

Rx-ID: 35686527 View in Reaxys 47/1037 Yield

Conditions & References Reaction Steps: 2 1.1: 18-crown-6 ether / acetone / 2 h / -30 - 0 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 2.1: dichloromethane-d2 / -78 - 20 °C / Inert atmosphere With 18-crown-6 ether in dichloromethane-d2, acetone Miyamoto, Kazunori; Suzuki, Mai; Suefuji, Takashi; Ochiai, Masahito; European Journal of Organic Chemistry; nb. 18; (2013); p. 3662 - 3666 View in Reaxys

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O S

O F

Rx-ID: 35686528 View in Reaxys 48/1037 Yield

Conditions & References Reaction Steps: 2 1.1: 18-crown-6 ether / acetone / 2 h / -30 - 0 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 2.1: n-butyllithium / dichloromethane-d2 / 0.5 h / -78 °C / Inert atmosphere With n-butyllithium, 18-crown-6 ether in dichloromethane-d2, acetone Miyamoto, Kazunori; Suzuki, Mai; Suefuji, Takashi; Ochiai, Masahito; European Journal of Organic Chemistry; nb. 18; (2013); p. 3662 - 3666 View in Reaxys

I O

Rx-ID: 35686542 View in Reaxys 49/1037 Yield

Conditions & References Reaction Steps: 3 1.1: dichloromethane 2.1: 18-crown-6 ether / acetone / 2 h / -30 - 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: n-butyllithium / dichloromethane-d2 / 0.5 h / -78 °C / Inert atmosphere With n-butyllithium, 18-crown-6 ether in dichloromethane, dichloromethane-d2, acetone Miyamoto, Kazunori; Suzuki, Mai; Suefuji, Takashi; Ochiai, Masahito; European Journal of Organic Chemistry; nb. 18; (2013); p. 3662 - 3666 View in Reaxys

N+

(v4)

(v3)

(v2) Au+ (v4) –

C–

(v2)

Au+

C– (v4)

Rx-ID: 35745925 View in Reaxys 50/1037 Yield

Conditions & References in benzene-d6, Time= 12h, T= 80 °C Noesel, Pascal; Lauterbach, Tobias; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.; Chemistry - A European Journal; vol. 19; nb. 26; (2013); p. 8634 - 8641 View in Reaxys

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-1 F

(v4)

B FF

O O

I+

O O

Rx-ID: 36064587 View in Reaxys 51/1037 Yield

Conditions & References With [Cu(dpphen)2](PF6), N-ethyl-N,N-diisopropylamine in acetonitrile, Time= 0.5h, T= 20 °C , Schlenk technique, Inert atmosphere, Irradiation Baralle, Alexandre; Fensterbank, Louis; Goddard, Jean-Philippe; Ollivier, Cyril; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10809 - 10813 View in Reaxys -1 F

(v4)

B FF

I+

F F

Rx-ID: 36064588 View in Reaxys 52/1037 Yield

F (v4)

B FF

O S +I

O O

Rx-ID: 36064589 View in Reaxys 53/1037 Yield

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F F

F (v4)

C–

N+

I Cl

C–

Au+ (v2) (v4)

(v1)

–Cl

(v3)

(v4) Au3+ Cl –

C–

(v1)

(v4)

F F

Rx-ID: 36770207 View in Reaxys 54/1037 Yield

Conditions & References

75 %

in chloroform, Time= 3h, T= 45 °C , Inert atmosphere Ghidiu, Michael J.; Pistner, Allen J.; Yap, Glenn P. A.; Lutterman, Daniel A.; Rosenthal, Joel; Organometallics; vol. 32; nb. 18; (2013); p. 5026 - 5029 View in Reaxys

O O H 2N

O O

I O

N I O

Rx-ID: 36793880 View in Reaxys 55/1037 Yield

Conditions & References With iodine in chloroform-d1, Mechanism Yang, Hai-Tao; Ren, Wen-Long; Dong, Chun-Ping; Yang, Yang; Sun, Xiao-Qiang; Miao, Chun-Bao; Tetrahedron Letters; vol. 54; nb. 50; (2013); p. 6799 - 6803 View in Reaxys

Rx-ID: 848953 View in Reaxys 56/1037 Yield

Conditions & References With potassium iodate, sulfuric acid, iodine Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys With sulfuric acid, iodine, mercury(II) sulfate Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys With sodium persulfate, iodine, acetic acid Elbs; Jaroslawzew; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 92 View in Reaxys With mercury(I) sulfate, sulfuric acid, iodine

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Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys 4 %Chromat.

With cerium(IV) oxide, dihydrogen peroxide, iodine in water, Time= 10h, pH= 3, Reflux Zhang, Peng; Sun, Dongqing; Wen, Mingwei; Yang, Jingkui; Zhou, Kebin; Wang, Zhixiang; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 720 - 729 View in Reaxys -1 F (v4)

H N

B FF

NH I+

Rx-ID: 32439496 View in Reaxys 57/1037 Yield 78 %

Conditions & References With sodium hydroxide, Time= 10h, T= 80 °C , under air, regioselective reaction Wen, Jun; Zhang, Ruo-Yi; Chen, Shan-Yong; Zhang, Ji; Yu, Xiao-Qi; Journal of Organic Chemistry; vol. 77; nb. 1; (2012); p. 766 - 771 View in Reaxys

O–

H N

I+ O

S F

F O

Rx-ID: 32439497 View in Reaxys 58/1037 Yield 78 %

I+ H N

Br–

Rx-ID: 32439502 View in Reaxys 59/1037 Yield 77 %

I 2H

Rx-ID: 32600698 View in Reaxys 60/1037 Yield 23 %Chromat.

Conditions & References Stage 1: in tetrahydrofuran, toluene, Time= 24h, T= 60 °C , Inert atmosphere Stage 2: With water-d2 in tetrahydrofuran

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Shirakawa, Eiji; Hayashi, Yumi; Itoh, Ken-Ichi; Watabe, Ryo; Uchiyama, Nanase; Konagaya, Wataru; Masui, Seiji; Hayashi, Tamio; Angewandte Chemie - International Edition; vol. 51; nb. 1; (2012); p. 218 - 221 View in Reaxys

Rx-ID: 32869203 View in Reaxys 61/1037 Yield

Conditions & References

7 %Chromat.

With cerium(IV) oxide, dihydrogen peroxide, iodine in water, pH= 4.5, Reflux Zhang, Peng; Sun, Dongqing; Wen, Mingwei; Yang, Jingkui; Zhou, Kebin; Wang, Zhixiang; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 720 - 729 View in Reaxys

O F

S O

Rx-ID: 33010539 View in Reaxys 62/1037 Yield

Conditions & References With tetrabutyl ammonium fluoride, iodine in monoethylene glycol diethyl ether, Time= 16h, T= 20 °C , Inert atmosphere Rodriguez-Lojo, Diego; Cobas, Agustin; Pena, Diego; Perez, Dolores; Guitian, Enrique; Organic Letters; vol. 14; nb. 6; (2012); p. 1363 - 1365 View in Reaxys

F F

(v1)

F F

F B

F F

Rx-ID: 33116760 View in Reaxys 63/1037 Yield

Conditions & References

90 %Spectr. With air in dimethyl sulfoxide, Time= 12h, T= 20 °C Qi, Qingqing; Shen, Qilong; Lu, Long; Journal of the American Chemical Society; vol. 134; nb. 15; (2012); p. 6548 - 6551 View in Reaxys

F F

(v1)

F F

F B

I F F

F F

Rx-ID: 33116761 View in Reaxys 64/1037 Yield

Conditions & References

45 %Spectr. With air in dimethyl sulfoxide, Time= 15h, T= 20 °C Qi, Qingqing; Shen, Qilong; Lu, Long; Journal of the American Chemical Society; vol. 134; nb. 15; (2012); p. 6548 - 6551 View in Reaxys

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F F

Rx-ID: 33116768 View in Reaxys 65/1037 Yield

Conditions & References With copper in dimethyl sulfoxide, N,N-dimethyl-formamide, Time= 12h, T= 20 °C Qi, Qingqing; Shen, Qilong; Lu, Long; Journal of the American Chemical Society; vol. 134; nb. 15; (2012); p. 6548 - 6551 View in Reaxys

Rx-ID: 33116773 View in Reaxys 66/1037 Yield

Conditions & References Stage 1: With copper(I) bromide in diethyl ether, Time= 0.5h, T= -10 - 0 °C Stage 2: With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane in dimethyl sulfoxide, Time= 4h, T= -10 - 20 °C , Inert atmosphere Qi, Qingqing; Shen, Qilong; Lu, Long; Journal of the American Chemical Society; vol. 134; nb. 15; (2012); p. 6548 - 6551 View in Reaxys O I

I O

Rx-ID: 33465238 View in Reaxys 67/1037 Yield

Conditions & References

69 %

4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil. Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C Stage 2: in tetrahydrofuran, hexane, Time= 3h, T= -78 °C Stage 3: With ethanol, iodine, potassium carbonate in tetrahydrofuran, hexane, Time= 16h, T= -78 - 20 °C Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; nb. 24; (2012); p. 4701 - 4709 View in Reaxys

P Cl

Rx-ID: 33678642 View in Reaxys 68/1037 Yield 64 %

Conditions & References in diethyl ether, T= -60 °C Prishchenko, Andrey A.; Livantsov, Mikhail V.; Novikova, Olga P.; Livantsova, Ludmila I.; Petrosyan, Valery S.; Heteroatom Chemistry; vol. 23; nb. 4; (2012); p. 352 - 372 View in Reaxys

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O P

Rx-ID: 33678643 View in Reaxys 69/1037 Yield

Conditions & References

61 %

in diethyl ether, Time= 1h, T= -60 °C Prishchenko, Andrey A.; Livantsov, Mikhail V.; Novikova, Olga P.; Livantsova, Ludmila I.; Petrosyan, Valery S.; Heteroatom Chemistry; vol. 23; nb. 4; (2012); p. 352 - 372 View in Reaxys

O I

Rx-ID: 33753230 View in Reaxys 70/1037 Yield

Conditions & References With dipotassium peroxodisulfate, silver(I) acetate in acetonitrile, Time= 24h, T= 100 °C Seo, Sangwon; Taylor, John B.; Greaney, Michael F.; Chemical Communications; vol. 48; nb. 66; (2012); p. 8270 - 8272 View in Reaxys

O I

Rx-ID: 34167160 View in Reaxys 71/1037 Yield

Conditions & References With boron trifluoride diethyl etherate in dichloromethane, Time= 2h, T= -25 °C , Inert atmosphere Khatri, Hem Raj; Zhu, Jianglong; Chemistry - A European Journal; vol. 18; nb. 39; (2012); p. 12232 - 12236 View in Reaxys I

Rx-ID: 34167178 View in Reaxys 72/1037 Yield

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F F

F O O

I O

F F

Rx-ID: 34167179 View in Reaxys 73/1037 Yield

F F

S O

O O F

O S O

O–

P+

O F

F F

Rx-ID: 34500212 View in Reaxys 74/1037 Yield

Conditions & References in chloroform-d1 Pell, Thomas P.; Couchman, Shannon A.; Ibrahim, Sara; Wilson, David J. D.; Smith, Brian J.; Barnard, Peter J.; Dutton, Jason L.; Inorganic Chemistry; vol. 51; nb. 23; (2012); p. 13034 - 13040 View in Reaxys

I O

2 P

N+

O–

N+

F F

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N+

O O

O–

N+

Rx-ID: 34500213 View in Reaxys 75/1037 Yield

Conditions & References

86 %

in dichloromethane, Time= 0.5h, Glovebox, Inert atmosphere Pell, Thomas P.; Couchman, Shannon A.; Ibrahim, Sara; Wilson, David J. D.; Smith, Brian J.; Barnard, Peter J.; Dutton, Jason L.; Inorganic Chemistry; vol. 51; nb. 23; (2012); p. 13034 - 13040 View in Reaxys

O–

N+ I

S N+

N+

N+ O–

Rx-ID: 34500219 View in Reaxys 76/1037 Yield

Conditions & References Reaction Steps: 2 1: [D3]acetonitrile / Glovebox; Inert atmosphere 2: [D3]acetonitrile / Glovebox; Inert atmosphere in [D3]acetonitrile Pell, Thomas P.; Couchman, Shannon A.; Ibrahim, Sara; Wilson, David J. D.; Smith, Brian J.; Barnard, Peter J.; Dutton, Jason L.; Inorganic Chemistry; vol. 51; nb. 23; (2012); p. 13034 - 13040 View in Reaxys

N C

N+

O–

I O

N+

F N

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O O

N+

O–

F F

Rx-ID: 34500221 View in Reaxys 77/1037 Yield

Conditions & References in [D3]acetonitrile, Glovebox, Inert atmosphere Pell, Thomas P.; Couchman, Shannon A.; Ibrahim, Sara; Wilson, David J. D.; Smith, Brian J.; Barnard, Peter J.; Dutton, Jason L.; Inorganic Chemistry; vol. 51; nb. 23; (2012); p. 13034 - 13040 View in Reaxys

O–

I+

F O

Rx-ID: 34538000 View in Reaxys 78/1037 Yield

Conditions & References With potassium thiocyanate, T= 120 °C , Inert atmosphere Vaddula, Buchi Reddy; Varma, Rajender S.; Leazer, John; European Journal of Organic Chemistry; nb. 35; (2012); p. 6852 6855 View in Reaxys

I I

Rx-ID: 29546785 View in Reaxys 79/1037 Yield

Conditions & References 1 :Comparative Example 1; In the system shown in FIG. 1, benzene (26.4 g/hr) and iodine (42.9 g/hr) were fed into a reactor without adding monoiodobenzene, and were subjected to a continuous iodination process under conditions of a reaction temperature of 280° C. and atmospheric pressure. 24 hours after the reaction conditions were reached, sampling and analysis were performed. The experimental conditions and results are shown in Table 1 below. With iodine, oxygen, zeolite catalyst, Time= 24h, T= 280 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; US2010/185031; (2010); (A1) English View in Reaxys 3 :Example 3; In the equipment as shown in Fig. 2, benzene (91.3 g/hr), iodine (47.87 g/hr), and monoiodo benzene (422.7 g/hr) were introduced to perform iodination in the presence of Na-13X zeolite catalyst under the same conditions as in Comparative Example 1. In addition, diiodo benzene (162.2 g/hr) was also introduced, and the composition of diiodo benzene was 22percent (wtpercent), based on the total feed materials. At this time, the molar ratio of non-halogenated aromatic compound/iodine introduced was 1.93. Further, a temperature distribution graph according to a length of the reactor, measured at the center of the reactor in the same manner as in Comparative Example 1, is shown in Fig. 4. The reaction conditions and data of the reaction products are shown in the following Table 1. In particular, all areas of the reactor were maintained at an almost constant temperature. The temperature of the upper part of the reactor was maintained at approximately 300 °C or lower, which is close to the desired temperature. The reaction temperature was also maintained at approximately 275 °C or higher along with the flow direction of the reactant. With iodine, oxygen, Na-13X zeolite, T= 275 - 300 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK Chemicals, Co., Ltd.; EP2374778; (2011); (A2) English View in Reaxys

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F O

S O

Rx-ID: 30320529 View in Reaxys 80/1037 Yield

Conditions & References Stage 1: With potassium fluoride, 18-crown-6 ether, tri-n-butyl-tin hydride, hydroquinone in tetrahydrofuran, Time= 2h, T= 20 °C , Inert atmosphere Stage 2: With iodine in dichloromethane, Time= 2h, T= 20 °C , Inert atmosphere, Stille coupling Lakshmi, B. Vasantha; Wefelscheid, Ulrike K.; Kazmaier, Uli; Synlett; nb. 3; (2011); p. 345 - 348; Art.No: G36110ST View in Reaxys

O O

C I

O –O

O+

Rx-ID: 30874327 View in Reaxys 81/1037 Yield

Conditions & References

87 %, 9 %Chromat.

in acetone, T= 35 °C , In carbon dioxide atmosphere Tanaseichuk; Pryanichnikova; Burtasov; Lisina; Dolganov; Russian Journal of Organic Chemistry; vol. 47; nb. 3; (2011); p. 442 - 445 View in Reaxys

C OH

I O

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O –O

O+

O O

Rx-ID: 30874328 View in Reaxys 82/1037 Yield

Conditions & References T= 60 °C , In carbon dioxide atmosphere Tanaseichuk; Pryanichnikova; Burtasov; Lisina; Dolganov; Russian Journal of Organic Chemistry; vol. 47; nb. 3; (2011); p. 442 - 445 View in Reaxys

O I

S O

Rx-ID: 9295766 View in Reaxys 83/1037 Yield 94 %

Conditions & References With Cu(II) salen-acetate in acetonitrile, Time= 3.5h, T= 20 °C Sun, Wei; Herdtweck, Eberhardt; Kuehn, Fritz E.; New Journal of Chemistry; vol. 29; nb. 12; (2005); p. 1577 - 1580 View in Reaxys With C21H35Cl2CuN6O9 in acetonitrile, Time= 7h, T= 25 °C Comba, Peter; Merz, Michael; Pritzkow, Hans; European Journal of Inorganic Chemistry; nb. 9; (2003); p. 1711 - 1718 View in Reaxys

15 %Chromat.

With [Ir(δ5-pentamethylcyclopentadienyl)(2-phenylene-δC1δ-pyridine-δN)(OH2)][trifluoromethanesulfonate] in dichloromethane, Time= 12h, T= 0 °C , Inert atmosphere Sau, Yiu-Keung; Yi, Xiao-Yi; Chan, Ka-Wang; Lai, Chun-Sing; Williams, Ian D.; Leung, Wa-Hung; Journal of Organometallic Chemistry; vol. 695; nb. 9; (2010); p. 1399 - 1404 View in Reaxys

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I I

Rx-ID: 28961927 View in Reaxys 84/1037 Yield

Conditions & References Stage 1: With diethylzinc, phosphazene base-P4-tert-butyl in hexane, N,N-dimethyl acetamide, Time= 24h, T= 20 °C , Inert atmosphere Stage 2: With methanol in hexane, N,N-dimethyl acetamide Naka, Hiroshi; Ito, Keisuke; Ueno, Masahiro; Kobayashi, Koji; Kondo, Yoshinori; New Journal of Chemistry; vol. 34; nb. 8; (2010); p. 1700 - 1706 View in Reaxys Stage 1: With isopropylmagnesium chloride in tetrahydrofuran, T= -30 - -20 °C Stage 2: With water, ammonium chloride, Time= 0.0833333h Cvengro, Alcohols Jan; Stolz, Daniel; Togni, Antonio; Synthesis; nb. 16; (2009); p. 2818 - 2824 View in Reaxys O –B

K+

Rx-ID: 29204498 View in Reaxys 85/1037 Yield

Conditions & References With chloroamine-T, sodium iodide in tetrahydrofuran, water, Time= 0.333333h, T= 20 °C Akula, Murthy R.; Yao, Min-Liang; Kabalka, George W.; Tetrahedron Letters; vol. 51; nb. 8; (2010); p. 1170 - 1171 View in Reaxys O I O

Rx-ID: 29825395 View in Reaxys 86/1037 Yield

Conditions & References 9 :EXAMPLE 9; A solution of Kryptofix 2.2.2 (40 Ornol) in acetonitrile ( 1 mL) was added to a solution of KF (25 Qmol) in water (0.1 mL). The solvents were evaporated at 120° C and the residue was dried by azeotropic distillation with acetonitrile (3 X 1 mL). A solution of the phenyliodonium ylide precursor in dry dimethylformamide (1.0 mL) was added to the dried KFKryptofix complex and the reaction vessel was hermetically sealed. The reaction mixture was heated at 1300C for 15 min. The reaction mixture was cooled to room temperature and processed with a silica gel chromatography column (12 X 1 cm). The products of the reaction were eluted off the column with diethyl ether (20 mL) and analyzed by GC/MS (30 m X 0.25 mm J;W Scientific DB-5MS capillary column; Varian Saturn 2000 mass spectrometer) and by analytical HPLC (Phenomenex Luna Cl 8 column, 5μ particle size, 250 X 4.6 mm; eluent : methanol/water = 75/25; flow rate : 1 mL/min; UV detection at 254 nm).[0046] The products observed by GC/MS and analytical HPLC in these reactions are summarized in Figure 4.[0047] In each of these reactions with the fluoride ion, only three major aromatic products were observed - substitution of the nucleophile on the aromatic ring to yield a fluoroaryl derivative, substitution of hydrogen on the aromatic ring to give the arene and formation of an iodoaryl analog. GC/MS analysis conclusively proved the identity of these products. Analytical HPLC data supported the GC/MS data. The GC/MS analysis showed that the nucleophile (i.e. fluoride) did not substitute on the dione moiety to yield l-fluoro-2,2-dimethyl-l,3-dioxane-4,6-dione (13) (Figure 5, Path B) but instead the fluoride substituted regiospecifically on the phenyl ring on the ipso carbon. This observation can be rationalized by the presence of a delocalized negative charge distributed over the dione part of the dioxane ring system which would repel the nucleophile (i.e. fluoride ion) also carrying a negative charge.; On the other hand, the carbon atom on the aromatic ring carrying the positively charged iodine moiety has an electron deficiency and makes itself a more favorable point for the attack by the nucleophile to yield the fluoroaryl derivative (Figure 5, Path A). Substitution of hydrogen on the aromatic ring to give the hydrocarbon derivatives (i.e. benzene, toluene, mesitylene, anisole etc) strongly indicate involvement of a competing radical pathway for this nucleophilic substitution reaction and abstraction of hydrogen from the solvent. Such a radical pathway has previously been observed in the nucleophilic reaction of fluoride with the closely related iodonium salts (M. Van Der Puy, "Conversion of Diaryiodonium Salts to Aryl Fluorides." J. Flourine Chem. 21. pp 385-392 (1982)). Thus, when the trimethyl substituted iodonium ylide (10b) reaction was conducted in a deuterated solvent (e.g. DMF-d&7)

GC/MS analysis showed the presence of deutereomesitylene (Figure 4) in the product mixture indicating a radical channel competing with the nucleophilic substitution reaction.

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With potassium fluoride, [2.2.2]cryptande in N,N-dimethyl-formamide, Time= 0.25h, T= 130 °C , sealed tube, Reactivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SATYAMURTHY, Nagichettiar; BARRIO, Jorge, R.; WO2010/117435; (2010); (A2) English View in Reaxys O O

S HO

Rx-ID: 29852036 View in Reaxys 87/1037 Yield

Conditions & References Stage 1: With 2-Iodobenzoic acid, 3-chloro-benzenecarboperoxoic acid in acetonitrile, Time= 1.5h, T= 20 °C Stage 2: With iodine in acetonitrile, Time= 8h, Darkness, Reflux Suzuki, Yuhsuke; Ishiwata, Yoshihide; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron Letters; vol. 51; nb. 45; (2010); p. 5950 - 5953 View in Reaxys O

O S I

O N O I

S S

O H 2N

S O

O O

N O

Rx-ID: 29907412 View in Reaxys 88/1037 Yield 14 %, 40 %

Conditions & References With iodine in dichloromethane, T= 20 °C , Inert atmosphere Lamar, Angus A.; Nicholas, Kenneth M.; Journal of Organic Chemistry; vol. 75; nb. 22; (2010); p. 7644 - 7650 View in Reaxys O

O S I

O N O

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H 2N

N O

O O N O

Rx-ID: 29907413 View in Reaxys 89/1037 Yield 17 %

Conditions & References With iodine in 1,2-dichloro-ethane, T= 75 °C , Inert atmosphere Lamar, Angus A.; Nicholas, Kenneth M.; Journal of Organic Chemistry; vol. 75; nb. 22; (2010); p. 7644 - 7650 View in Reaxys

O I

S O

O O S

Rx-ID: 29907414 View in Reaxys 90/1037 Yield 63 %

O S I

O N O O

H 2N

S O

O O

Rx-ID: 29907416 View in Reaxys 91/1037 Yield

Conditions & References Stage 1: With iodine in dichloromethane-d2, Time= 0.5h, T= 20 °C Stage 2: in dichloromethane-d2, T= 20 °C Lamar, Angus A.; Nicholas, Kenneth M.; Journal of Organic Chemistry; vol. 75; nb. 22; (2010); p. 7644 - 7650 View in Reaxys

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S I

O S

O N

Rx-ID: 29907417 View in Reaxys 92/1037 Yield 97 %

O I

S O

O S

H 2N

S O

Rx-ID: 29907418 View in Reaxys 93/1037 Yield 78 %

O S I

O N O O

O S

H 2N

N O

Rx-ID: 29907419 View in Reaxys 94/1037 Yield 73 %

O S I

O N O

44/330

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O S O

H 2N

N O

Rx-ID: 29907420 View in Reaxys 95/1037 Yield 50 %

O S I

O N O

O O S

O H 2N

S O

O N O

N O

Rx-ID: 29907421 View in Reaxys 96/1037 Yield 24 %

O I

S O

O O

H 2N

S O

Rx-ID: 29907422 View in Reaxys 97/1037 Yield 72 %

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O S I

O N O

O O H 2N

N O

Rx-ID: 29907423 View in Reaxys 98/1037 Yield 60 %

O S I

O N O

O S

O H 2N

S O

O N O

N O

Rx-ID: 29907424 View in Reaxys 99/1037 Yield 57 %

O I

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O O

H 2N

S N H

S O

Rx-ID: 29907426 View in Reaxys 100/1037 Yield 78 %

O I

S O

S NH

H 2N

I O

O O

Rx-ID: 29907427 View in Reaxys 101/1037 Yield

O S I

O N O

H 2N

S O

O N O

Rx-ID: 29907430 View in Reaxys 102/1037 Yield 20 %

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O S I

O N O O

O S

O H 2N

N O

Rx-ID: 29907432 View in Reaxys 103/1037 Yield

Conditions & References

13 %

With iodine in dichloromethane, T= 20 °C , Inert atmosphere Lamar, Angus A.; Nicholas, Kenneth M.; Journal of Organic Chemistry; vol. 75; nb. 22; (2010); p. 7644 - 7650 View in Reaxys O

O S I

N O

O N O O

O S

O H 2N

N O

Rx-ID: 29907433 View in Reaxys 104/1037 Yield

Conditions & References

80 %

With iodine in dichloromethane, T= 20 °C , Inert atmosphere Lamar, Angus A.; Nicholas, Kenneth M.; Journal of Organic Chemistry; vol. 75; nb. 22; (2010); p. 7644 - 7650 View in Reaxys O

O S I

O N O

I O

H 2N

S O

O N

S NH

O N O

Rx-ID: 29907434 View in Reaxys 105/1037

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Yield

B HO

F F

Rx-ID: 29941046 View in Reaxys 106/1037 Yield

Conditions & References

11 %Chromat., 37 %Chromat., 5 %Chromat.

With potassium fluoride, potassium phosphate, copper(l) iodide, 1,10-Phenanthroline in N,N-dimethyl-formamide, Time= 4h, T= 70 °C Chu, Lingling; Qing, Feng-Ling; Organic Letters; vol. 12; nb. 21; (2010); p. 5060 - 5063 View in Reaxys

-1

I+

F F

Na +

–O

(v6)

F F

I+

F O–

F F

Rx-ID: 30058323 View in Reaxys 107/1037 Yield

Conditions & References in acetonitrile, T= 20 °C , Darkness Wang, Bijia; Cerny, Ronald L.; Uppaluri, Shriharsha; Kempinger, Jayson J.; Dimagno, Stephen G.; Journal of Fluorine Chemistry; vol. 131; nb. 11; (2010); p. 1113 - 1121 View in Reaxys

-1

I+ F F

(v6)

F F

Rx-ID: 30058328 View in Reaxys 108/1037 Yield

Conditions & References With tetramethylammonium fluoride in benzene-d6, T= 80 °C , Darkness Wang, Bijia; Cerny, Ronald L.; Uppaluri, Shriharsha; Kempinger, Jayson J.; Dimagno, Stephen G.; Journal of Fluorine Chemistry; vol. 131; nb. 11; (2010); p. 1113 - 1121 View in Reaxys

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(v2)

(v4)

Rx-ID: 31328080 View in Reaxys 109/1037 Yield

Conditions & References With N-iodo-succinimide in benzene-d6, T= 20 °C , chemoselective reaction Hashmi, A. Stephen K.; Ramamurthi, Tanuja Dondeti; Todd, Matthew H.; Tsang, Althea S.-K.; Graf, Katharina; Australian Journal of Chemistry; vol. 63; nb. 12; (2010); p. 1619 - 1626 View in Reaxys

O O O

Rx-ID: 1995040 View in Reaxys 110/1037 Yield

Conditions & References With p-benzylphenol in methanol, Time= 0.666667h, T= 20 °C , further reagents, Product distribution, Mechanism Pelter, Andrew; Elgendy, Said M. A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 16; (1993); p. 1891 - 1896 View in Reaxys With C22H26IrN in acetonitrile, Time= 1h, T= 45 °C Park-Gehrke, Lisa S.; Freudenthal, John; Kaminsky, Werner; Dipasquale, Antonio G.; Mayer, James M.; Dalton Transactions; nb. 11; (2009); p. 1972 - 1983 View in Reaxys F

F O O O

I I

Rx-ID: 20860880 View in Reaxys 111/1037 Yield

Conditions & References Reaction Steps: 2 1: 62 percent / acetonitrile / 24 h / Ambient temperature 2: I2 / CH2Cl2 / 6 h / Heating With iodine in dichloromethane, acetonitrile Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys Reaction Steps: 2 1: 60 percent / acetonitrile / 24 h / Ambient temperature 2: I2 / CH2Cl2 / 6 h / Heating

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With iodine in dichloromethane, acetonitrile Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys Reaction Steps: 2 1: 95 percent / acetonitrile / 24 h / Ambient temperature 2: I2 / benzene / 6 h / Heating With iodine in acetonitrile, benzene Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys Reaction Steps: 2 1: 67 percent / acetonitrile / 24 h / 0 °C 2: I2 / CH2Cl2 / 6 h / Heating With iodine in dichloromethane, acetonitrile Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys Reaction Steps: 2 1: 74 percent / acetonitrile / 24 h / 0 °C 2: I2 / CH2Cl2 / 6 h / Heating With iodine in dichloromethane, acetonitrile Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys Reaction Steps: 2 1: 94 percent / acetonitrile / 24 h / Ambient temperature 2: I2 / CH2Cl2 / 6 h / Heating With iodine in dichloromethane, acetonitrile Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys With dihydrogen peroxide, sodium hydrogencarbonate in water, T= 20 °C Catir, Mustafa; Kilic, Hamdullah; Nardello-Rataj, Veronique; Aubry, Jean-Marie; Kazaz, Cavit; Journal of Organic Chemistry; vol. 74; nb. 12; (2009); p. 4560 - 4564 View in Reaxys

Rx-ID: 28241045 View in Reaxys 112/1037 Yield

Conditions & References in tetrahydrofuran, biphenyl, pentane, T= -50.16 °C , Inert atmosphere, Equilibrium constant Gorecka-Kobylinska, Joanna; Schlosser, Manfred; Journal of Organic Chemistry; vol. 74; nb. 1; (2009); p. 222 - 229 View in Reaxys

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Rx-ID: 28241047 View in Reaxys 113/1037 Yield

Rx-ID: 28241048 View in Reaxys 114/1037 Yield

I I

tri-iodobenzene

Rx-ID: 28440326 View in Reaxys 115/1037 Yield

Conditions & References 1; 5; 6 :In the system shown in FIG. 1, benzene (26.4 g/hr) and iodine (42.9 g/hr) were fed into a reactor without adding monoiodobenzene, and were subjected to a continuous iodination process under conditions of a reaction temperature of 280 °C and atmospheric pressure. 24 hours after the reaction conditions were reached, sampling and analysis were performed. The experimental conditions and results are shown in Table 1 below. With iodine, oxygen, Time= 24 - 400h, T= 280 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2009/54555; (2009); (A1) English View in Reaxys

I I

Rx-ID: 28519056 View in Reaxys 116/1037 Yield

Conditions & References 1 :Comparative Example 1; The iodinating reactor shown in Fig. 1 was used, and without adding DIB, only the benzene (176.4g/ hr), iodine (I2) (275.0g/hr), and air were reacted. The iodine (I2) and the air went through the preheater and were heated to 200°C and then supplied to the iodinating reactor (ROl). Further, benzene was also heated to 200°C and supplied in the form of a vapor, using the other feeding line. The reaction temperature of the iodinating reactor was controlled by controlling the temperature of oil supplied to the oil jacket. And the temperature of the iodinating reactor, which was measured at the inner center of the reactor, was adjusted to be constant at 280°C. Nevertheless, the reaction temperature was not maintained constantly. The temperature of the upper part of the iodinating reactor was higher <n="19"/>than preferable. And, the temperature of the iodinating reactor went down along with the flow direction of the reactant. To examine temperature profile of the iodinating reactor, a temperature measuring instrument such as a thermowell and a thermocouple was installed at the inner center of the iodinating reactor. The temperature of the upper, middle, and lower parts of the iodinating reactor was then periodically examined using the movable

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thermocouple, which can move upward and downward of the iodinating reactor to determine the highest temperature region. The reaction was carried out in the normal temperature for 24 hours after reaching the reaction condition. Then, sampling and analyzing were conducted after the iodination, and the reaction conditions and results are shown in the following Table 1.; Example 1; <n="20"/>The iodinating reactor shown in Fig. 2 was used, and except that the benzene (565.2g/hr), di-iodo benzene (83.4g/ hr), and iodine (I2) (900.1g/hr) were supplied to the iodinating reactor (ROl), all of the reaction conditions were adjusted to be the same as in Comparative example 1. The reaction conditions and reaction results are shown in the following Table 1. The used DIB was obtained from a mother liquor of three kinds of isomers (p-, o~, and nr) , which was separated from pure crystallized solid p-DIB. With iodine, oxygen, zeolite catalyst, Time= 24h, T= 25 - 280 °C , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2009/78667; (2009); (A2) English View in Reaxys 2 :Example 2; Except that the benzene, water, and iodine (I2) were supplied at 550.0g/hr, 35g/hr, and 744.1g/hr, respectively, all of the reaction conditions were adjusted to be the same as in Comparative Example 1. The reaction conditions and the reaction results are shown in the following Table 1. With iodine, oxygen, zeolite catalyst in water, Time= 24h, T= 25 - 280 °C , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2009/78667; (2009); (A2) English View in Reaxys F F F O O

O HO

Rx-ID: 28660371 View in Reaxys 117/1037 Yield

Conditions & References T= -35 °C , optical yield given as percent ee Catir, Mustafa; Kilic, Hamdullah; Nardello-Rataj, Veronique; Aubry, Jean-Marie; Kazaz, Cavit; Journal of Organic Chemistry; vol. 74; nb. 12; (2009); p. 4560 - 4564 View in Reaxys O

O S

B HO

Rx-ID: 28752925 View in Reaxys 118/1037 Yield

Conditions & References With air, iodine, potassium carbonate, polyethylene glycol 400, Time= 12h, T= 140 °C , Suzuki-Miyaura coupling Mao, Jincheng; Hua, Qiongqiong; Xie, Guanlei; Guo, Jun; Yao, Zhigang; Shi, Daqing; Ji, Shunjun; Advanced Synthesis and Catalysis; vol. 351; nb. 4; (2009); p. 635 - 641 View in Reaxys

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O S O– I+

O S

O–

O O K+

K+

S O–

Rx-ID: 29053152 View in Reaxys 119/1037 Yield

Conditions & References With potassium tert-butylate in tetrahydrofuran, T= 20 °C Justik, Michael W.; Protasiewicz, John D.; Updegraff, James B.; Tetrahedron Letters; vol. 50; nb. 44; (2009); p. 6072 - 6075 View in Reaxys -1

F (v4)

B FF

-1

(v4)

I+

O F

P+ O

Rx-ID: 29110011 View in Reaxys 120/1037 Yield

Conditions & References in dichloromethane, Heating Matveeva, Elena D.; Podrugina, Tatyana A.; Pavlova, Anna S.; Mironov, Andrey V.; Borisenko, Anatoliy A.; Gleiter, Rolf; Zefirov, Nikolay S.; Journal of Organic Chemistry; vol. 74; nb. 24; (2009); p. 9428 - 9432 View in Reaxys -1 F (v4)

B FF

I N+

Rx-ID: 2287718 View in Reaxys 121/1037 Yield

Conditions & References With potassium iodide in water, acetone, Substitution Grishchuk; Gorbovoi; Zagrichuk; Ganushchak; Kudrik; Russian Journal of General Chemistry; vol. 69; nb. 8; (1999); p. 1299 - 1303 View in Reaxys With iodine, potassium iodide in dimethyl sulfoxide, T= 15 °C Citterio, Attilio; Arnold, Anna; Synthetic Communications; vol. 11; nb. 8; (1981); p. 639 - 642 View in Reaxys With iodide in water, Irradiation, δ: 313 nm, Quantum yield

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Devoe, R. J.; Sahyun, M. R. V.; Serpone, N.; Sharma, D. K.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2342 - 2349 View in Reaxys With [emim][I], [emim][Tf2N], Time= 24h, T= 24.84 °C Bini, Riccardo; Chiappe, Cinzia; Marmugi, Elisa; Pieraccini, Daniela; Chemical Communications; nb. 8; (2006); p. 897 899 View in Reaxys With trimethylsilyl iodide, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, Time= 2h, T= 65 °C Hubbard, Abigail; Okazaki, Takao; Laali, Kenneth K.; Journal of Organic Chemistry; vol. 73; nb. 1; (2008); p. 316 - 319 View in Reaxys

I I

Rx-ID: 28134547 View in Reaxys 122/1037 Yield

Conditions & References 1 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HY(Si/Al molar ratio is 5), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 4 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HBeta(Si/Al molar ratio is 25), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 3 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HX, Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 2; 5; 6; 7; 8 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to

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MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity.; Examples 5 and 6, and Comparative Example 5To investigate the effect of transiodination temperature, these examples were evaluated substantially the same as Example 2 except that the transiodination temperatures were 1200C (Example 5), 180°C (Example 6), and 100 "C (Comparative Example 5). The selectivities to MIB with the passage of reaction time were measured and are shown in Fig. 2.As shown in Fig. 2, when the reaction temperature was lower the selectivity to MIB was higher, but the catalyst activity decreased rapidly due to coke deposited in the catalyst. That is, when the temperature was lower than 120 "C (Comparative Example 5), the catalyst activity decreased rapidly with the passage of the reaction time. On the other hand, when the temperature was at 120 0C or higher (Examples 5), the initial selectivity to MIB began to decrease slowly. When the reaction was performed for a long time at 180 0C or higher (Example 6), the catalyst activity did not decrease.; Examples 7 and 8. and Comparative Examples 6 and 7 To investigate the effect of feed composition, these examples were evaluated substantially the same as the Example 2 except that the feeds were Reactant 1 (Example 7), Reactant 2 (Example 8), Reactant 3 (Comparative Example 6), and Reactant 4 (Comparative Example 7). The selectivity to MIB with the passage of reaction time were measured and shown in Fig. 3.As seen from Fig. 3, the reactants of Examples 7 and 8 with molar ratios of benzene/Feed of 2:1 or higher showed superior selectivity to MIB with no catalyst inactivation. However, the reactants of Comparative Examples 6 and 7 with molar ratios of benzene/Feed of lower than 2:1 showed low selectivity toMIB and a decrease of catalyst activity with the passage of reaction time. With HY(Si/Al molar ratio is 12), Time= 8 - 200h, T= 100 - 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 3 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HY(Si/Al molar ratio is 80), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 1 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With HZCM-5 (Si/Al molar ratio is 25), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 2 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With Na-ZCM-5 (Si/Al molar ratio is 25), Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 9 :Example 9The transiodination in Example 7 was performed until the catalyst was inactivated. Then, the inactivated catalyst was recycled by calcining at 4850C for 12 hours in an air atmosphere. The transiodination was carried out with recycled catalyst

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under the same conditions as of Example 7.The selectivities to MIB in Example 7 using a fresh catalyst and Example 9 using the recycled catalyst are shown in Fig. 4. As shown in Fig. 4, the selectivity to MIB in Example 7 was maintained consistently at 90percent or more for up to 80 hours of reaction time, but decreased slowly after 80 hours, which was similar to the selectivity of Example 9 using the recycled catalyst.These examples confirmed that the recycling of the catalyst caused the catalyst activity to be recovered. The recovery efficiency of the catalyst was very high, and thus the catalyst can be reused several times without detrimental <n="15"/>effects.The preparation method of the present invention is advantageous in recovering iodine from m-diiodo benzene, o-di-iodo benzene, and tri-iodo benzene, which are obtained in general production of p-di-iodo benzene as byproducts, while minimizing the loss of iodine. With inactivated HY(Si/Al molar ratio is 12); calcined at 485 C for 12h, Time= 200h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys 2 :Examples 1 to 4. and Comparative Examples 1 to 42g of a catalyst described in Table 2 and Reactant 1 of Table 1 were input at a feed speed of 2 ml/hr and reacted at 180 °C , 1 atm. The reaction products after the passage of reaction time were collected, and the components were analyzed and the results are shown in Table 2.Table 2 <n="13"/>*(numerical value) represents Si/AI molar ratio.As seen from Table 1 , HY-type zeolite and HBeta-type zeolite showed superior activity and selectivity to MIB to HZSM-5, HX, and HL type zeolite. As the Si/AI molar ratio of HY zeolite catalyst increased, the selectivity toMIB increased and showed maximum catalytic activity at a Si/AI molar ratio of 10 or higher with less loss of catalyst activity with the passage of reaction time. HZSM-5, alumina, and an X type of zeolite showed very low catalytic activity. With aluminum oxide, Time= 8h, T= 180 °C , p= 760.051Torr , Product distribution / selectivity Patent; SK CHEMICALS CO., LTD.; WO2008/82082; (2008); (A1) English View in Reaxys

O I

S O

O N

N H 2N

S O

Rx-ID: 28455370 View in Reaxys 123/1037 Yield

Conditions & References With zinc dibromide in benzene, T= 20 - 50 °C , Inert atmosphere, Molecular sieve Kalita, Biswajit; Lamar, Angus A.; Nicholas, Kenneth M.; Chemical Communications; nb. 36; (2008); p. 4291 - 4293 View in Reaxys

O –

S O S

O S F O

S O

O S

Rx-ID: 11110052 View in Reaxys 124/1037

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Yield

Conditions & References With cesium fluoride, Further byproducts. Carroll, Michael A.; Jones, Clare; Tang, Shu-Ling; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 50; nb. 5-6; (2007); p. 450 - 451 View in Reaxys O

F I+ F

B–

Rx-ID: 11234205 View in Reaxys 125/1037 Yield

Conditions & References With BrNBu4 in chloroform, T= 55 °C Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys O

I+ F

B–

HO F

F F

F O

Rx-ID: 11234206 View in Reaxys 126/1037 Yield 23 % Chromat., 4 % Chromat., 24 % Chromat.

Conditions & References Time= 90h, T= 130 °C , Product distribution, Further Variations: reaction time Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys O

F I+

B– F

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O O

Rx-ID: 11234207 View in Reaxys 127/1037 Yield

Conditions & References Time= 45h, T= 130 °C , Product distribution, Further Variations: reaction time Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys O

I+ F

B–

HO F

F O

F F

Rx-ID: 11234208 View in Reaxys 128/1037 Yield

Conditions & References Time= 166h, T= 130 °C , Product distribution, Further Variations: reaction time Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys -1 F (v4)

F HO

B FF

F +I

F I

F F

Rx-ID: 11234209 View in Reaxys 129/1037 Yield

Conditions & References Time= 340h, T= 130 °C , Product distribution, Further Variations: reaction time Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys

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F I+ B–

Rx-ID: 11234210 View in Reaxys 130/1037 Yield

F I+

B–

Rx-ID: 11234211 View in Reaxys 131/1037 Yield

Conditions & References Time= 22h, T= 130 °C , Product distribution, Further Variations: reaction time Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys -1

F (v4)

B FF

Rx-ID: 11234212 View in Reaxys 132/1037 Yield

Conditions & References With BrNBu4 in chloroform, T= 55 °C Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys

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-1 F (v4)

B FF

Rx-ID: 11234213 View in Reaxys 133/1037 Yield

Conditions & References Time= 164h, T= 130 °C , Product distribution, Further Variations: reaction time Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys -1 F (v4)

B FF

Rx-ID: 11246017 View in Reaxys 134/1037 Yield

Conditions & References Irradiation, Product distribution Slegt, Micha; Minne, Floor; Zuilhof, Han; Overkleeft, Hermen S.; Lodder, Gerrit; European Journal of Organic Chemistry; nb. 32; (2007); p. 5353 - 5363 View in Reaxys

F B–

HO F

F F

I O

Rx-ID: 11246020 View in Reaxys 135/1037 Yield

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O O O

I O

Rx-ID: 28659627 View in Reaxys 136/1037 Yield

Conditions & References

21 %

With dipotassium peroxodisulfate, sulfuric acid, iodine in 1,2-dichloro-ethane, Time= 20h, T= 40 °C Hossain, Md. Delwar; Kitamura, Tsugio; Bulletin of the Chemical Society of Japan; vol. 80; nb. 11; (2007); p. 2213 - 2219 View in Reaxys

Rx-ID: 6585455 View in Reaxys 137/1037 Yield

Conditions & References 2 : Preparation of iodobenzene EXAMPLE 2 Preparation of iodobenzene A phenyldiazonium sulfate solution prepared from 93 parts by weight of aniline, 153 parts by weight of concentrated sulfuric acid, 600 parts by weight of water and 69 parts by weight of sodium nitrite is run in the course of 30 minutes, at 40° C, into a solution of 375 parts by weight of water, 66 parts by weight of concentrated sulfuric acid, 166 parts by weight of potassium iodide and 75 parts by weight of an aqueous 40percent strength sodium bisulfite solution, the latter only being added just before the diazonium salt solution is run in. The mixture is stirred for 30 minutes at 40° C and then for 60 minutes at from 75° to 80° C, after which it is cooled to from 20° to 30° C. The iodobenzene is removed from the aqueous phase by extraction with 200 parts by weight of benzene. Distillation under reduced pressure gives first runnings of benzene, followed by 167 parts by weight of iodobenzene, of boiling point 67° C/12 mm Hg. Yield 85percent of theory. Patent; BASF Aktiengesellschaft; US4007221; (1977); (A) English View in Reaxys Guenther,H.; Chemische Berichte; vol. 96; (1963); p. 1801 - 1809 View in Reaxys Wirth,H.O. et al.; Justus Liebigs Annalen der Chemie; vol. 634; (1960); p. 84 - 104 View in Reaxys Blum,J. et al.; Journal of Organic Chemistry; vol. 33; nb. 5; (1968); p. 1928 - 1930 View in Reaxys Wiegand,G.H.; McEwen,W.E.; Journal of Organic Chemistry; vol. 33; (1968); p. 2671 - 2675 View in Reaxys Ptitsyna,O.A. et al.; Zhurnal Organicheskoi Khimii; vol. 5; nb. 3; (1969); p. 401 - 411,390 - 399 View in Reaxys Wittig; Hoffmann; Chemische Berichte; vol. 95; (1962); p. 2729,2733 View in Reaxys Neiland; Wanag; Doklady Chemistry; vol. 130; (1960); p. 19; Doklady Akademii Nauk SSSR; vol. 130; (1960); p. 90; ; nb. 10897; (1960) View in Reaxys McKillop et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 4841 View in Reaxys Cookson; Farquharson; Tetrahedron Letters; (1979); p. 1255 View in Reaxys Rahman; Gilman; Journal of the Indian Chemical Society; vol. 51; (1974); p. 1018 View in Reaxys Takagi et al.; Chemistry Letters; (1978); p. 191 View in Reaxys Fridman; Mendeleev Chemistry Journal; vol. 22; (1977); p. 26; ; p. 110 View in Reaxys

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Hoizumi; Moriya; Journal of Labelled Compounds; vol. 10; (1974); p. 499,502 View in Reaxys Baird; Surridge; Journal of Organic Chemistry; vol. 35; (1970); p. 3436,3439 View in Reaxys Uemura et al.; Bulletin of the Chemical Society of Japan; vol. 47; (1974); p. 147 View in Reaxys Johnson; Sherwood; Australian Journal of Chemistry; vol. 24; (1971); p. 2281,2283, 2284-2286 View in Reaxys Patent; BASF; DE2503504; (1975); ; vol. 85; nb. 123549 View in Reaxys Taylor et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 2351,2353, 2354 View in Reaxys Patent; US-Landwirtschaftsministerium; US3666820; (1972); ; vol. 77; nb. 100728b View in Reaxys Dyall; Kemp; Australian Journal of Chemistry; vol. 26; (1973); p. 1969,1970,1971 View in Reaxys Snegur; Manulkin; J. Gen. Chem. USSR (Engl. Transl.); vol. 39; (1969); p. 1310,1281 View in Reaxys Afanas'ew et al.; Zhurnal Organicheskoi Khimii; vol. 2; (1966); p. 423,421 View in Reaxys Nesmeyanov et al.; Doklady Chemistry; vol. 235; (1977); p. 425; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 235; (1977); p. 591 View in Reaxys McLachlan; McCarthy; Journal of the American Chemical Society; vol. 84; (1962); p. 2519 View in Reaxys Kampmeier; Hoffmeister; Journal of the American Chemical Society; vol. 84; (1962); p. 3787 View in Reaxys Lodotschnikowa et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 946,940 View in Reaxys Minisci; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1307,1315 View in Reaxys Kurz; Hage; Journal of Organic Chemistry; vol. 42; (1977); p. 4080 View in Reaxys Koser; Yu; Journal of Organic Chemistry; vol. 41; (1976); p. 125,127,128 View in Reaxys Bhattacharya; Raj; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 15; (1977); p. 799 View in Reaxys Miller et al.; Journal of the American Chemical Society; vol. 92; (1970); p. 2821,2822, 2825 View in Reaxys Bunce; Murray; Tetrahedron; vol. 27; (1971); p. 5323,5332 View in Reaxys Kameo; Manabe; Nippon Kagaku Kaishi; (1974); p. 195 View in Reaxys Kabalka; Ferrell; Synthetic Communications; vol. 9; (1979); p. 443,446, 447 View in Reaxys Milas; Plesnicar; Journal of the American Chemical Society; vol. 90; (1968); p. 4450 View in Reaxys Miller; Tetrahedron Letters; (1968); p. 1831 View in Reaxys Nilsson; Wennerstroem; Tetrahedron Letters; (1968); p. 3307 View in Reaxys Ogata; Aoki; Journal of the American Chemical Society; vol. 90; (1968); p. 6187 View in Reaxys McKillop et al.; Tetrahedron Letters; (1969); p. 2427 View in Reaxys Bernstein; Justus Liebigs Annalen der Chemie; vol. 702; (1967); p. 8 View in Reaxys Silbert et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 3670 View in Reaxys Pticyna et al.; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 708,695 View in Reaxys

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Beringer; Bodlaender; Journal of Organic Chemistry; vol. 34; (1969); p. 1981 View in Reaxys I : Diphenylethyltinhydroxide having formula 2 of the formula sheet. EXAMPLE I Diphenylethyltinhydroxide having formula 2 of the formula sheet. A solution of 16.5 g of iodine in 115 ml of diethyl ether was added dropwise in 30 minutes at 0° C. to a solution of 24.5 g of triphenylethyltin in 100 ml of diethyl ether. After standing for 24 hours at 0° C., the reaction mixture was filtered and concentrated under reduced pressure. Next, under highly reduced pressure (0.6-0.7 mm Hg), the iodobenzene formed was distilled off. Patent; Nederlandse Centrale Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek; US4547320; (1985); (A) English View in Reaxys 1 : EXAMPLE 1 The yields are in terms of the molar yield on the basis of the charged diphenyl iodonium bromide. The second-stage reaction was carried out by adding 164 g. of ammonium persulfate to a solution of 92 g. of the iodobenzene recovered as above and 70 g. of benzene in 74percent by weight of aqueous sulfuric acid cooled to -10° C. and stirring the resulting mixture for 20 hours. Patent; Nippon Petrochemicals Company, Limited; US4554360; (1985); (A) English View in Reaxys In addition, the following benzene derivatives are useful as monomeric substances of the present invention: ... benzylmethylether, benzylamine, thiophenol, bromobenzene, iodobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, ... Patent; Hiratsuka, Atsunori; Yano, Kazuyoshi; Karube, Isao; Tsai, Shuo-Wen; Yokoyama, Kenji; Koide, Satoshi; Akimoto, Takuo; US2006/113189; (2006); (A1) English View in Reaxys -1 F (v4)

B FF

Rx-ID: 10131141 View in Reaxys 138/1037 Yield

Conditions & References

20 % Chromat., 5.2 % Chromat., 16.8 % Chromat.

in methanol, Time= 1.5h, Photolysis, Further byproducts given Slegt, Micha; Gronheid, Roel; Van Vlugt, Dennis Der; Ochiai, Masahito; Okuyama, Tadashi; Zuilhof, Han; Overkleeft, Hermen S.; Lodder, Gerrit; Journal of Organic Chemistry; vol. 71; nb. 6; (2006); p. 2227 - 2235 View in Reaxys

-1 F

(v4)

B FF

I+

Rx-ID: 10149069 View in Reaxys 139/1037

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Yield

Conditions & References

38 % Chromat., 19 % Chromat., 61 % Chromat.

F O

I S O

F O

Rx-ID: 10201232 View in Reaxys 140/1037 Yield

Conditions & References

6 % Chromat.

With 3-chloroprop-1-ene, trifluoroacetic acid, zinc, CoBr2(2,2δ-bipyridine) in pyridine, dodecane, acetonitrile, Time= 8h, T= 50 °C , Title compound not separated from byproducts Kazmierski, Igor; Gosmini, Corinne; Paris, Jean-Marc; Perichon, Jacques; Synlett; nb. 6; (2006); p. 881 - 884 View in Reaxys

Rx-ID: 10223620 View in Reaxys 141/1037 Yield

Conditions & References

15 % Chromat., 3 % Chromat.

With 3-chloroprop-1-ene, trifluoroacetic acid, zinc, CoBr2(2,2δ-bipyridine) in pyridine, dodecane, acetonitrile, Time= 5h, T= 50 °C , Title compound not separated from byproducts Kazmierski, Igor; Gosmini, Corinne; Paris, Jean-Marc; Perichon, Jacques; Synlett; nb. 6; (2006); p. 881 - 884 View in Reaxys

O O O

O O

Rx-ID: 10289063 View in Reaxys 142/1037 Yield 61 %

Conditions & References With ruthenium trichloride, water in acetonitrile, Time= 0.0833333h, T= 20 °C Yusubov, Mekhman S.; Chi, Ki-Whan; Park, Joo Yeon; Karimov, Rashad; Zhdankin, Viktor V.; Tetrahedron Letters; vol. 47; nb. 35; (2006); p. 6305 - 6308 View in Reaxys

H 2N

Rx-ID: 10299770 View in Reaxys 143/1037 Yield

Conditions & References With cetyltrimethylammonim bromide, potassium iodide, sodium nitrite in water, T= 0 - 5 °C Mishra; Panigrahi; Misra, Pramila K.; Behera; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 45; nb. 9; (2006); p. 2140 - 2142 View in Reaxys

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O O

N F

N–

F F F

O F

O O O

N–

N+

F F F

Rx-ID: 23753894 View in Reaxys 144/1037 Yield

Conditions & References

73 %

9 : Synthesis of 1-methyl-3-(2',2',2'-trifluoroethyl)imidazolium bis(trifluoromethanesulfonyl)imide (compound 9) using compound 7 (2,2,2-Trifluoroethyl)(phenyl)iodonium bis(trifluoromethanesulfonyl)imide (compound 7) (3.4 g, 6 mmol) and methylene chloride (12 ml) were placed in a reaction vessel to convert the inside of the reaction vessel to a nitrogen atmosphere. While stirring and cooling in an ice bath, 1-methylimidazole (0.49 g, 6 mmol) was added dropwise thereto over the course of 1 minute. After the dropwise addition thereof, the ice bath was removed, and the mixture was allowed to react at room temperature for 3 hours. After the completion of the reaction, the solvent was removed by distillation. The resulting liquid product was washed with water and then with hexane in order to remove a side product, iodobenzene. Subsequently, this liquid product was dissolved in a small amount of ethyl acetate, and a large amount of ether was added thereto to separate the liquid product. The liquid product was separated from the solvent and then dried at 110° C. under reduced pressure using a vacuum pump. Thus, pure 1-methyl-3-(2',2',2'-trifluoroethyl)imidazolium bis(trifluoromethanesulfonyl)imide (compound 9) was obtained as a liquid substance (yield 1.94 g, 73percent). When the product is colored, it may be subjected to decolorization with active carbon. Physical property, elemental analysis and spectral data of the compound 9 are shown in Table 8. in dichloromethane, Time= 3h, T= 0 - 20 °C , Product distribution / selectivity Patent; TOYOTA JIDOSHA KABUSHIKI KAISHA; US2006/94882; (2006); (A1) English View in Reaxys O

S I+

O–

HO O

O OH

I S

O S

Rx-ID: 25920797 View in Reaxys 145/1037 Yield 92 %

Conditions & References With lithium hydroxide, tri-tert-butyl phosphine, palladium diacetate in 1,2-dimethoxyethane, water, Time= 5h, T= 20 °C , Suzuki-type coupling Kazantzi, Georgia; Malamidou-Xenikaki, Elizabeth; Spyroudis, Spyros; Synlett; nb. 16; (2006); p. 2597 - 2600 View in Reaxys

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I+ O –O

Rx-ID: 9786615 View in Reaxys 146/1037 Yield

Conditions & References

45 %

With sodium nitrite in chloroform, water, Time= 72h, Product distribution Woltermann, Christopher J.; Shechter, Harold; Helvetica Chimica Acta; vol. 88; nb. 2; (2005); p. 354 - 369 View in Reaxys -1

(v4)

B FF

I+

Rx-ID: 9812209 View in Reaxys 147/1037 Yield

Conditions & References With tetrabutylammomium bromide, tetrabutylammonium perchlorate in chloroform, T= 60 °C , Kinetics Fujita, Morifumi; Wan, Hyeok Kim; Fujiwara, Koji; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 480 - 488 View in Reaxys With tetrabutylammomium bromide, tetrabutylammonium perchlorate in chloroform, T= 60 °C Fujita, Morifumi; Wan, Hyeok Kim; Fujiwara, Koji; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 480 - 488 View in Reaxys

B O

Rx-ID: 9879594 View in Reaxys 148/1037 Yield

Conditions & References With chloroamine-T, sodium iodide in tetrahydrofuran, Time= 0.166667h Thompson, Alicia L. S.; Kabalka, George W.; Akula, Murthy R.; Huffman, John W.; Synthesis; nb. 4; (2005); p. 547 - 550; Art.No: M05304SS View in Reaxys

I Sn

Rx-ID: 9913642 View in Reaxys 149/1037 Yield

Conditions & References With iodine in chloroform-d1 Lucke, Andrew J.; Young, David J.; Journal of Organic Chemistry; vol. 70; nb. 9; (2005); p. 3579 - 3583

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View in Reaxys O

O S

O I

S O

Rx-ID: 10109415 View in Reaxys 150/1037 Yield 88 %

Conditions & References With Cu(II) salen-acetate in acetonitrile, Time= 24h, T= 20 °C Sun, Wei; Herdtweck, Eberhardt; Kuehn, Fritz E.; New Journal of Chemistry; vol. 29; nb. 12; (2005); p. 1577 - 1580 View in Reaxys

O I

S O

I N

S O O

Rx-ID: 10110439 View in Reaxys 151/1037 Yield 82 %

Conditions & References With Cu(II) salen-acetate in acetonitrile, Time= 6.5h, T= 20 °C Sun, Wei; Herdtweck, Eberhardt; Kuehn, Fritz E.; New Journal of Chemistry; vol. 29; nb. 12; (2005); p. 1577 - 1580 View in Reaxys

O I

S O

Rx-ID: 10114980 View in Reaxys 152/1037 Yield 22 %

Conditions & References With Cu(II) salen-acetate in acetonitrile, Time= 20h, T= 20 °C Sun, Wei; Herdtweck, Eberhardt; Kuehn, Fritz E.; New Journal of Chemistry; vol. 29; nb. 12; (2005); p. 1577 - 1580 View in Reaxys

O I

S O

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I N S O

Rx-ID: 10116957 View in Reaxys 153/1037 Yield

Conditions & References

84 %

With Cu(II) salen-acetate in acetonitrile, Time= 1h, T= 20 °C Sun, Wei; Herdtweck, Eberhardt; Kuehn, Fritz E.; New Journal of Chemistry; vol. 29; nb. 12; (2005); p. 1577 - 1580 View in Reaxys

O I

S O O O

S N

Rx-ID: 10156111 View in Reaxys 154/1037 Yield

Conditions & References

76 %

With Cu(II) salen-acetate in acetonitrile, Time= 3h, T= 20 °C Sun, Wei; Herdtweck, Eberhardt; Kuehn, Fritz E.; New Journal of Chemistry; vol. 29; nb. 12; (2005); p. 1577 - 1580 View in Reaxys

F O

4-CF3C6H4COCr(CO)5(1-)NMe4 (1+)

S O

F O

Rx-ID: 13044685 View in Reaxys 155/1037 Yield

Conditions & References Reaction Steps: 2 1: KOAc / PdCl2(dppf) / dimethylsulfoxide / 3 h / 80 °C 2: 58 percent / aq. NaI; chloramine-T / tetrahydrofuran / 0.17 h With potassium acetate, chloroamine-T, sodium iodide, (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran, dimethyl sulfoxide Thompson, Alicia L. S.; Kabalka, George W.; Akula, Murthy R.; Huffman, John W.; Synthesis; nb. 4; (2005); p. 547 - 550; Art.No: M05304SS View in Reaxys

2-chlorobenzylhalide

4-CF3C6H4COCr(CO)5(1-)NMe4 (1+) Rx-ID: 13062415 View in Reaxys 156/1037

Yield

Conditions & References Reaction Steps: 3 1: 98 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C 2: KOAc / PdCl2(dppf) / dimethylsulfoxide / 3 h / 80 °C 3: 58 percent / aq. NaI; chloramine-T / tetrahydrofuran / 0.17 h

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With pyridine, potassium acetate, chloroamine-T, sodium iodide, (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran, dichloromethane, dimethyl sulfoxide Thompson, Alicia L. S.; Kabalka, George W.; Akula, Murthy R.; Huffman, John W.; Synthesis; nb. 4; (2005); p. 547 - 550; Art.No: M05304SS View in Reaxys

O–

I+ O

F O

Rx-ID: 23498309 View in Reaxys 157/1037 Yield

Conditions & References 1 :Experimental; A solution of the potassium fluoride (5.8mg, 0. 1 mmol), 2,2, 2-Kryptofix (37.6mg, 0. 1 mmol), in D3-acetonitrile (0. 5ml) was prepared in an NMR tube. To this was added and diphenyl iodonium triflate (43mg, 0. 1mmol) in D3-acetonitrile (0. 5ml). The NMR's of the mixture were run (1H, 13C and 19F NMR) and compared with the 1H 13C and 19F NMR (as appropriate) of the individual starting components. This indicated that on mixing of the components there was an immediate reaction converting the iodonium triflate to the fluoride. The reaction mixture was then heated to 80°C for 60 min on an oil bath. The sample was removed from the hot oil, cooled to room temperature by plunging in cold water and the 1H 13C and 19F NMR determined. 1H, C and 19F NMR (as appropriate) of fluorobenzene, iodobenzene and benzene in D3 acetonitrile were also run. Results >From these NMR experiments it was clear that fluoride ion reacts immediately with the iodonium salt to give a compound which is completely different from the trifluoromethane salt. This compound was relatively stable at room temperature but slowly reacted. On heating the reaction the complex formed on mixing was converted to a mixture of benzene and iodobenzene. Conclusion The NMR data indicated that the first step of the reaction was rapid at room temperature with the iodonium ion disappearing immediately. The resulting intermediate (assumed to be the fluoride) was converted on heating to iodobenzene and benzene in what must be a reduction reaction... With potassium fluoride, [2.2.2]cryptande in [D3]acetonitrile, Time= 1h, T= 80 °C , Product distribution / selectivity Patent; GE HEALTHCARE LIMITED; WO2005/61415; (2005); (A1) English View in Reaxys

O–

I+ O

F F

Rx-ID: 23498310 View in Reaxys 158/1037 Yield

Conditions & References 2 :Experimental The method of Example 5 was repeated with the addition to the reaction mixture of TEMPO (3.12mg, 0.002 mmol). Results >From these NMR experiments it was clear that fluoride ion reacts immediately with the iodonium salt to give a compound which is completely different from the trifluoromethane salt. This is identical to the previous reaction without TEMPO. The reaction was relatively stable at room temperature but slowly reacts. On heating the reaction the complex formed on mixing was converted to a mixture of fluorobenzene and iodobenzene. Conclusion The NMR data indicated that the first step of the reaction was rapid at room temperature with the iodonium ion disappearing immediately. The resulting intermediatewas converted on heating to iodobenzene and fluorobenzene. The complete change in the course of the reaction on addition of TEMPO suggests that the reaction that converts the iodonium salt to benzene and iodobenzene is suppressed by the presence of a free radical terminator. With potassium fluoride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [2.2.2]cryptande in [D3]acetonitrile, Product distribution / selectivity Patent; GE HEALTHCARE LIMITED; WO2005/61415; (2005); (A1) English View in Reaxys F

B–

K+

Rx-ID: 9547354 View in Reaxys 159/1037

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Yield

Conditions & References With chloroamine-T, sodium iodide in tetrahydrofuran, water, Time= 0.166667h, T= 20 °C Kabalka, George W.; Mereddy, Arjun R.; Tetrahedron Letters; vol. 45; nb. 2; (2004); p. 343 - 345 View in Reaxys -1 F (v4)

C–

B FF

N+ +I

Rx-ID: 9318769 View in Reaxys 160/1037 Yield

Conditions & References

2 %, 3 %, 64 %

With methanol in chloroform, Time= 1h, T= 60 °C Fujita, Morifumi; Kim, Wan Hyeok; Okuyama, Tadashi; Chemistry Letters; vol. 32; nb. 4; (2003); p. 382 - 383 View in Reaxys O

I O

Rx-ID: 9323619 View in Reaxys 161/1037 Yield

Conditions & References

33 %, 5 %

With dirhodium tetraacetate in dichloromethane, T= 20 °C , Product distribution Mueller, Paul; Allenbach, Yves; Robert, Estelle; Tetrahedron Asymmetry; vol. 14; nb. 7; (2003); p. 779 - 785 View in Reaxys

O O O

O P

Na +

O O–

OH O

P O

O P O

O O

Rx-ID: 9390214 View in Reaxys 162/1037 Yield 90 %, 90 %

Conditions & References With sodium hydride in tetrahydrofuran, Time= 1h, T= 20 °C Makowiec, Slawomir; Rachon, Janusz; Heteroatom Chemistry; vol. 14; nb. 4; (2003); p. 352 - 359 View in Reaxys

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-1 F (v4)

B FF

I+

Rx-ID: 9401482 View in Reaxys 163/1037 Yield

Conditions & References

9 % Chromat., 91 % Chromat.

With tetrahydrofuran, tri(sec-butyl)borane, Time= 3h, T= 20 °C , Product distribution Ochiai, Masahito; Tsuchimoto, Yoshimi; Hayashi, Takanori; Tetrahedron Letters; vol. 44; nb. 29; (2003); p. 5381 - 5384 View in Reaxys

-1 F (v4)

B FF

I+

Rx-ID: 9401483 View in Reaxys 164/1037 Yield

Conditions & References

3 % Chromat., 97 % Chromat.

With tetrahydrofuran, tri(sec-butyl)borane, Time= 3.5h, T= 20 °C , Product distribution Ochiai, Masahito; Tsuchimoto, Yoshimi; Hayashi, Takanori; Tetrahedron Letters; vol. 44; nb. 29; (2003); p. 5381 - 5384 View in Reaxys

-1 F (v4)

B FF

I+

Rx-ID: 9403620 View in Reaxys 165/1037 Yield

Conditions & References

82 % Chromat.

With tetrahydrofuran, tri(sec-butyl)borane, Time= 1h, T= 20 °C , Product distribution, Further Variations: Reagents, add. of 2phenylethanol Ochiai, Masahito; Tsuchimoto, Yoshimi; Hayashi, Takanori; Tetrahedron Letters; vol. 44; nb. 29; (2003); p. 5381 - 5384 View in Reaxys

-1 F (v4)

B FF

Cl I Cl

Rx-ID: 9414296 View in Reaxys 166/1037

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Yield

Conditions & References

17 % Chromat., 48 % Chromat.

With tetrahydrofuran, tri(sec-butyl)borane, Time= 2h, T= 20 °C , Product distribution Ochiai, Masahito; Tsuchimoto, Yoshimi; Hayashi, Takanori; Tetrahedron Letters; vol. 44; nb. 29; (2003); p. 5381 - 5384 View in Reaxys -1

F (v4)

B FF

I I

I+

Rx-ID: 9416200 View in Reaxys 167/1037 Yield

Conditions & References

1 % Chromat., 94 % Chromat.

-1 F (v4)

B FF

I+

Rx-ID: 9417853 View in Reaxys 168/1037 Yield

Conditions & References

60 % Chromat.

I+ Cl – I

18F

Rx-ID: 9435215 View in Reaxys 169/1037 Yield

Conditions & References With [18F]-potassium fluoride in N,N-dimethyl-formamide, Time= 0.666667h, T= 140 °C , Title compound not separated from byproducts Wuest, Frank R.; Kniess, Torsten; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 46; nb. 8; (2003); p. 699 713 View in Reaxys

I+

18F

F F

O–

Rx-ID: 9437261 View in Reaxys 170/1037 Yield

Conditions & References With [18F]-potassium fluoride in N,N-dimethyl-formamide, Time= 0.0833333h, microwave irradiation, Title compound not separated from byproducts Wuest, Frank R.; Kniess, Torsten; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 46; nb. 8; (2003); p. 699 713

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View in Reaxys

I+

O O

S O–

18F

Rx-ID: 9437469 View in Reaxys 171/1037 Yield

I+

O O

S O–

18F

Rx-ID: 9437679 View in Reaxys 172/1037 Yield

[(t-Bu)3P](Ph)PdI

Rx-ID: 9504637 View in Reaxys 173/1037 Yield

Conditions & References in benzene-d6, T= 70 °C , Equilibrium constant Roy, Amy H.; Hartwig, John F.; Journal of the American Chemical Society; vol. 125; nb. 46; (2003); p. 13944 - 13945 View in Reaxys O O

I I

Rx-ID: 9059252 View in Reaxys 174/1037 Yield 6 % Chromat.

Conditions & References With potassium tert-butylate in dimethyl sulfoxide, Irradiation Baumgartner, Maria T.; Jimenez, Liliana B.; Pierini, Adriana B.; Rossi, Roberto A.; Journal of the Chemical Society. Perkin Transactions 2; nb. 6; (2002); p. 1092 - 1097 View in Reaxys

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H N O

N H

I O O

Rx-ID: 9080763 View in Reaxys 175/1037 Yield

Conditions & References Stage 1: With bis-[(trifluoroacetoxy)iodo]benzene in dichloromethane, T= 20 °C Stage 2: With boron trifluoride diethyl etherate in dichloromethane, Further stages. Title compound not separated from byproducts. Prata, Jose V.; Clemente, Dina-Telma S.; Prabhakar, Sundaresan; Lobo, Ana M.; Mourato, Isabel; Branco, Paula S.; Journal of the Chemical Society. Perkin Transactions 1; nb. 4; (2002); p. 513 - 528 View in Reaxys

O I

Rx-ID: 9092142 View in Reaxys 176/1037 Yield

Conditions & References

31 % Chromat., 47 % Chromat.

With potassium tert-butylate in dimethyl sulfoxide, Time= 2h, Irradiation Baumgartner, Maria T.; Jimenez, Liliana B.; Pierini, Adriana B.; Rossi, Roberto A.; Journal of the Chemical Society. Perkin Transactions 2; nb. 6; (2002); p. 1092 - 1097 View in Reaxys -1 F (v4)

B FF

Rx-ID: 10274752 View in Reaxys 177/1037 Yield

Conditions & References With sodium acetate, Time= 2h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys -1 F (v4)

B FF

Rx-ID: 10284487 View in Reaxys 178/1037 Yield

Conditions & References With triethylamine, Time= 2h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137

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View in Reaxys -1

F F

(v4)

B FF

Rx-ID: 10285902 View in Reaxys 179/1037 Yield

–O

(v4)

B FF

N+

O O

Rx-ID: 10300088 View in Reaxys 180/1037 Yield

Conditions & References With acetic acid-d in chloroform, Time= 2h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys -1 F

–O

(v4)

B FF

N+

Rx-ID: 10300089 View in Reaxys 181/1037 Yield

Conditions & References With cyclohexene in chloroform, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys -1 F

O–

(v4)

S O

B FF

N+

O O

S O

Rx-ID: 10304835 View in Reaxys 182/1037 Yield 62 %, 28 %

Conditions & References in chloroform, Time= 5h, T= 60 °C

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Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys -1 F

O–

(v4)

S O

B FF

N+

O O O

Rx-ID: 10304836 View in Reaxys 183/1037 Yield

Conditions & References

62 %

With deuteromethanol in chloroform, Time= 5h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys -1

O– F

(v4)

O F

B FF

N+

O F

I F

S O F

F F

S O

O 13CH

F F

S O

Rx-ID: 10304927 View in Reaxys 184/1037 Yield

Conditions & References

28 %, 52 %

With d(4)-methanol in chloroform, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys -1

O– F

O S

O F

(v4)

B FF

N+

S O

Rx-ID: 10304928 View in Reaxys 185/1037 Yield

Conditions & References

20 %

in chloroform, Time= 6h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys

-1 O– F

F +I

S O

N+

(v4)

F F

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Rx-ID: 10304929 View in Reaxys 186/1037 Yield

Conditions & References Stage 1: in chloroform, T= 60 °C Stage 2: With sulfuric acid in methanol, water, Time= 9h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys

-1

(v4)

B FF

Rx-ID: 10333451 View in Reaxys 187/1037 Yield

Conditions & References in methanol, Time= 4h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys -1

F (v4)

B FF

Rx-ID: 10333452 View in Reaxys 188/1037 Yield

Conditions & References With sodium acetate in d(4)-methanol, Time= 1h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys F

O S

O S O O

O–

Rx-ID: 10333457 View in Reaxys 189/1037 Yield 28 % Chromat., 52 % Chromat.

Conditions & References in chloroform, Time= 10.5h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys

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-1 O

B F

I S

(v4)

F F

Rx-ID: 10333463 View in Reaxys 190/1037 Yield

Conditions & References

72 %, 15 %

With tetra-n-butylammonium 2,4,6-trimethylphenoxide in chloroform, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys

-1

F O

F +I

B F

(v4)

O S O

F F

Rx-ID: 10333464 View in Reaxys 191/1037 Yield

Conditions & References

34 %, 63 %

With tetrabutylammonium trifluoromethylsulfonate in chloroform, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8138 - 8146 View in Reaxys

-1 F +I

B F

(v4)

F F

I O

Rx-ID: 11004496 View in Reaxys 192/1037 Yield

Conditions & References in d(4)-methanol, Time= 3h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys

O -1 F +I

B F

(v4)

F F

Rx-ID: 11004501 View in Reaxys 193/1037 Yield 100 % Chromat.

Conditions & References With water in methanol, Time= 8h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137

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View in Reaxys

-1 F +

HO B F

(v4) O

F F

Rx-ID: 11004503 View in Reaxys 194/1037 Yield

Conditions & References

91 % Chromat.

With sodium acetate, Time= 2h, T= 60 °C Fujita, Morifumi; Sakanishi, Yuichi; Nishii, Masayoshi; Yamataka, Hiroshi; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 67; nb. 23; (2002); p. 8130 - 8137 View in Reaxys

H N H 2N

Mo(CO)6

Rx-ID: 14745871 View in Reaxys 195/1037 Yield

Conditions & References Reaction Steps: 2 1.1: 84 percent / sodium bicarbonate / CH2Cl2 / 20 °C 2.1: iodobenzene bistrifluoroacetate / CH2Cl2 / 20 °C 2.2: BF3*Et2O / CH2Cl2 With sodium hydrogencarbonate, bis-[(trifluoroacetoxy)iodo]benzene in dichloromethane Prata, Jose V.; Clemente, Dina-Telma S.; Prabhakar, Sundaresan; Lobo, Ana M.; Mourato, Isabel; Branco, Paula S.; Journal of the Chemical Society. Perkin Transactions 1; nb. 4; (2002); p. 513 - 528 View in Reaxys

Mo(CO)6

Rx-ID: 14749607 View in Reaxys 196/1037 Yield

Conditions & References Reaction Steps: 3 1.1: 89 percent / hydrazine hydrate / 110 - 120 °C 2.1: 84 percent / sodium bicarbonate / CH2Cl2 / 20 °C 3.1: iodobenzene bistrifluoroacetate / CH2Cl2 / 20 °C 3.2: BF3*Et2O / CH2Cl2 With sodium hydrogencarbonate, hydrazine hydrate, bis-[(trifluoroacetoxy)iodo]benzene in dichloromethane Prata, Jose V.; Clemente, Dina-Telma S.; Prabhakar, Sundaresan; Lobo, Ana M.; Mourato, Isabel; Branco, Paula S.; Journal of the Chemical Society. Perkin Transactions 1; nb. 4; (2002); p. 513 - 528 View in Reaxys

O H

Cl O NH 2

Rx-ID: 24078218 View in Reaxys 197/1037 Yield

Conditions & References 18 : EXAMPLE 18

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A mixture of this product (3.6 g), iodobenzene (Aldrich, 2.041 g) and dichlorobis(triphenylphosphine)palladium (II) (Aldrich, 70 mg), copper(I) iodide (Aldrich, 10 mg) and diethylamine (Aldrich, 60 mL) in a pressure bottle was purged with nitrogen and heated to 65° C. for 4 hours. The mixture was concentrated in vacuo. The residue was extracted with ethyl acetate and water. The organic extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography to provide the tert-butoxycarbonyl derivative of ethyl (3S)-3-amino-5-phenylpent-4-ynoate. This material was dissolved in 4 N HCL dioxane (Aldrich, 10 mL) and allowed to stand at 23° C. for 30 minutes. The volatiles were removed in vacuo to provide ethyl (3S)-3-amino-5-phenylpent-4-ynoate hydrochloride as colorless solid. 1H (DMSO-d6): δ 7.43 (5H, m); 4.61 1h, q); 4.13 (2H, q); 3.18 (1H, dd), 2.92 (1H, dd): 1.21 (3H, t). Patent; Rogers, Thomas; Clare, Michael; Lu, Hwang-Fun; Russell, Mark; Malecha, James W.; Khanna, Ish Kumar; Penning, Thomas; Nagarajan, Srinivasan Raj; US2002/99209; (2002); (A1) English View in Reaxys -1 F

(v4)

B FF

I I+

O O

Rx-ID: 4685671 View in Reaxys 198/1037 Yield

Conditions & References

51 %

Time= 28h, T= 50 °C Okuyama, Tadashi; Imamura, Shohei; Ishida, Yoshimi; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 543 - 548 View in Reaxys

50 % Chromat.

Time= 28h, T= 50 °C Okuyama; Ochiai; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4785 - 4786 View in Reaxys

O–

I+

F F

I O

Rx-ID: 4788605 View in Reaxys 199/1037 Yield 25 %

Conditions & References With hydrogenchloride, water, 1.) MeOH, room temperature, 16 h, Yield given. Multistep reaction. Further byproducts given Hinkle, Robert J.; Thomas, David B.; Journal of Organic Chemistry; vol. 62; nb. 22; (1997); p. 7534 - 7535 View in Reaxys

35 %, 25 %

Stage 1: in methanol, Time= 16h, T= 20 °C Stage 2: With hydrogenchloride, Further byproducts given McNeil; Hinkle; Rouse; Thomas; Journal of Organic Chemistry; vol. 66; nb. 16; (2001); p. 5556 - 5565 View in Reaxys

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-1 F (v4)

B FF

I+

I O

Rx-ID: 8802033 View in Reaxys 200/1037 Yield

Conditions & References With trifluoroacetic acid, T= 60 °C , Kinetics, Further Variations: Reagents, Temperatures, Solvents Okuyama, Tadashi; Imamura, Shohei; Ishida, Yoshimi; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 543 - 548 View in Reaxys -1 F (v4)

B FF

I I+

O O

Rx-ID: 8808641 View in Reaxys 201/1037 Yield

Conditions & References

14 %

Time= 6h, T= 50 °C , Further byproducts given Okuyama, Tadashi; Imamura, Shohei; Ishida, Yoshimi; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 543 - 548 View in Reaxys -1

F (v4)

B FF

I+

Rx-ID: 8823913 View in Reaxys 202/1037 Yield

Conditions & References

6.3 %, 79 % in methanol, water, Time= 20h, T= 50 °C Okuyama, Tadashi; Imamura, Shohei; Ishida, Yoshimi; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 543 - 548 View in Reaxys 7.7 %, 67 % in ethanol, water, Time= 15h, T= 50 °C Okuyama, Tadashi; Imamura, Shohei; Ishida, Yoshimi; Bulletin of the Chemical Society of Japan; vol. 74; nb. 3; (2001); p. 543 - 548 View in Reaxys

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N N

Rx-ID: 8838148 View in Reaxys 203/1037 Yield

Conditions & References With zinc(II) iodide in acetonitrile, Time= 2h, T= 20 °C Patrick, Timothy B.; Juehne, Thomas; Reeb, Elmer; Hennessy, Daniel; Tetrahedron Letters; vol. 42; nb. 21; (2001); p. 3553 - 3554 View in Reaxys O

S I

HO O

O S

O O

Rx-ID: 8864422 View in Reaxys 204/1037 Yield 61 %

Conditions & References Stage 1:Time= 0.333333h, T= 100 °C Stage 2: With toluene-4-sulfonic acid, Time= 4h, Heating Goff, Jeffrey M.; Justik, Michael W.; Koser, Gerald F.; Tetrahedron Letters; vol. 42; nb. 33; (2001); p. 5597 - 5599 View in Reaxys O

S I

HO O

O S

O O

Rx-ID: 8864450 View in Reaxys 205/1037 Yield 20 %

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S O

HO O

F F

S O

I F

Rx-ID: 8864451 View in Reaxys 206/1037 Yield 22 %

O O

HO O

O O

Rx-ID: 8864455 View in Reaxys 207/1037 Yield 30.5 %

S I

HO O

I O

O O

Rx-ID: 8864473 View in Reaxys 208/1037 Yield 56 %

Conditions & References Stage 1:Time= 0.333333h, T= 100 °C

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Stage 2: With toluene-4-sulfonic acid, Time= 4h, Heating Goff, Jeffrey M.; Justik, Michael W.; Koser, Gerald F.; Tetrahedron Letters; vol. 42; nb. 33; (2001); p. 5597 - 5599 View in Reaxys O

S I

O O

O S

O O

Rx-ID: 8864474 View in Reaxys 209/1037 Yield 41 %

S I

HO O

O O O

Rx-ID: 8864475 View in Reaxys 210/1037 Yield 64 %

HO O

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S I

I O

O O O

Rx-ID: 8864476 View in Reaxys 211/1037 Yield

Conditions & References

41 %

Stage 1:Time= 0.333333h, T= 100 °C Stage 2: With toluene-4-sulfonic acid, Time= 4h, Heating Goff, Jeffrey M.; Justik, Michael W.; Koser, Gerald F.; Tetrahedron Letters; vol. 42; nb. 33; (2001); p. 5597 - 5599 View in Reaxys

HO O

O S

I O

O O

Rx-ID: 8864477 View in Reaxys 212/1037 Yield 23 %

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S I

HO O

O O

Rx-ID: 8864499 View in Reaxys 213/1037 Yield 39 %

O O

I O O

Rx-ID: 8882673 View in Reaxys 214/1037 Yield 66 %

S I

HO O

O S O

O O

Rx-ID: 8890485 View in Reaxys 215/1037 Yield 73 %

Conditions & References Stage 1:Time= 0.333333h, T= 100 °C

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Stage 2: With toluene-4-sulfonic acid, Time= 4h, Heating Goff, Jeffrey M.; Justik, Michael W.; Koser, Gerald F.; Tetrahedron Letters; vol. 42; nb. 33; (2001); p. 5597 - 5599 View in Reaxys HO O

HO S O

O O

S O

Rx-ID: 8890486 View in Reaxys 216/1037 Yield

Conditions & References

66 %

O S

O HO

O O H

H O

O S

Rx-ID: 8890487 View in Reaxys 217/1037 Yield

Conditions & References

62 %

O–

I+

F F

I O

Rx-ID: 8897795 View in Reaxys 218/1037

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Yield

Conditions & References

35 %, 25 %

O I

H 2N

S O

Rx-ID: 8943660 View in Reaxys 219/1037 Yield

Conditions & References With (+)-2,2δ-isopropylidenebis[(4R)-4-phenyl-2-oxazoline], copper(II) bis(trifluoromethanesulfonate) in acetonitrile, T= 25 °C , Kinetics, Further Variations: Catalysts, Reagents Taylor, Sophia; Gullick, John; McMorn, Paul; Bethell, Donald; Page, Philip C. Bulman; Hancock, Frederick E.; King, Frank; Hutchings, Graham J.; Journal of the Chemical Society. Perkin Transactions 2; nb. 9; (2001); p. 1714 - 1723 View in Reaxys O

O S I

H 2N

I O

S O

N O

Rx-ID: 8959960 View in Reaxys 220/1037 Yield

F (v4)

B FF

I +I

Rx-ID: 8966556 View in Reaxys 221/1037 Yield

Conditions & References With sodium acetate in methanol, T= 25 °C , Kinetics Gronheid; Lodder; Ochiai; Sueda; Okuyama; Journal of the American Chemical Society; vol. 123; nb. 36; (2001); p. 8760 8765 View in Reaxys -1

F (v4)

B FF

I +I

Rx-ID: 8966557 View in Reaxys 222/1037 Yield

Conditions & References With sodium acetate in methanol, T= 25 °C , Kinetics

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Gronheid; Lodder; Ochiai; Sueda; Okuyama; Journal of the American Chemical Society; vol. 123; nb. 36; (2001); p. 8760 8765 View in Reaxys -1 F (v4)

B FF

I SH

I+

Rx-ID: 10196193 View in Reaxys 223/1037 Yield

Conditions & References

70 % Spectr.

in dichloromethane, Time= 20h, T= 20 °C Ochiai, Masahito; Yamamoto, Shinji; Suefuji, Takashi; Chen, Da-Wei; Organic Letters; vol. 3; nb. 17; (2001); p. 2753 2756 View in Reaxys -1 F

O–

(v4)

S O

B FF

N+

13CH

O O O

Rx-ID: 10304837 View in Reaxys 224/1037 Yield

Conditions & References

62 %

With metanol-d in chloroform, Time= 5h, T= 60 °C , Title compound not separated from byproducts Fujita; Sakanishi; Okuyama; Journal of the American Chemical Society; vol. 123; nb. 37; (2001); p. 9190 - 9191 View in Reaxys -1 F

O–

(v4)

S O

B FF

N+

13CH

O O

O H 13C

13C

13CH

S O

Rx-ID: 10304838 View in Reaxys 225/1037 Yield 58 %

Conditions & References in chloroform, Time= 5h, T= 60 °C Fujita; Sakanishi; Okuyama; Journal of the American Chemical Society; vol. 123; nb. 37; (2001); p. 9190 - 9191 View in Reaxys

I+ Cl –

HO Si

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Rx-ID: 8545699 View in Reaxys 226/1037 Yield

Conditions & References With δ-naphthol, Time= 0.0833333h, T= 20 °C , Photolysis, Decomposition, Product distribution, Further Variations: Reagents Gu, Haiyan; Zhang, Wenqin; Feng, Kesheng; Neckers, Douglas C.; Journal of Organic Chemistry; vol. 65; nb. 11; (2000); p. 3484 - 3488 View in Reaxys

NH 2

benzylaminomethylpolystyrene

Rx-ID: 8606797 View in Reaxys 227/1037 Yield

Conditions & References Stage 1: With tert.-butylnitrite, boron trifluoride diethyl etherate in dichloromethane, Diazotization Stage 2:Addition Stage 3: With trichlorosilane in dichloromethane, Time= 0.25h, T= 32 °C , Reduction Lormann, Matthias; Dahmen, Stefan; Braese, Stefan; Tetrahedron Letters; vol. 41; nb. 20; (2000); p. 3813 - 3816 View in Reaxys F

Si F

Rx-ID: 8622280 View in Reaxys 228/1037 Yield

Conditions & References With iodine, copper(l) chloride in N,N-dimethyl-formamide, Time= 24h, Iodination Nishihara, Yasushi; Ikegashira, Kazutaka; Toriyama, Fumihiko; Mori, Atsunori; Hiyama, Tamejiro; Bulletin of the Chemical Society of Japan; vol. 73; nb. 4; (2000); p. 985 - 990 View in Reaxys -1

F (v4)

B FF

I F

Cl I+

Rx-ID: 8627641 View in Reaxys 229/1037 Yield

Conditions & References

23 %, 24 %, in chloroform, Time= 336h, T= 60 °C , Thermolysis, Decomposition 29 % Okuyama, Tadashi; Fujita, Morifumi; Gronheid, Roel; Lodder, Gerrit; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5125 - 5129 View in Reaxys -1 F (v4)

B FF

I +I

Rx-ID: 8627647 View in Reaxys 230/1037

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Yield

Conditions & References

22 %, 22 %, in chloroform, Time= 15h, T= 60 °C , Thermolysis, Decomposition 39 % Okuyama, Tadashi; Fujita, Morifumi; Gronheid, Roel; Lodder, Gerrit; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5125 - 5129 View in Reaxys -1 F (v4)

B FF

I+

I F

Rx-ID: 8629077 View in Reaxys 231/1037 Yield

Conditions & References

3 %, 62 %

in chloroform, Time= 40h, T= 60 °C , Thermolysis, Decomposition Okuyama, Tadashi; Fujita, Morifumi; Gronheid, Roel; Lodder, Gerrit; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5125 - 5129 View in Reaxys

-1 F (v4)

B FF

I F

Rx-ID: 8656437 View in Reaxys 232/1037 Yield

Conditions & References

6.7 %, 12.3 %, 1.7 %

in chloroform, Time= 25h, T= 60 °C , Thermolysis, Decomposition, Product distribution, Further Variations: Reaction partners Okuyama, Tadashi; Fujita, Morifumi; Gronheid, Roel; Lodder, Gerrit; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5125 - 5129 View in Reaxys

-1 F

B F

(v4)

F F

I+

Rx-ID: 8729367 View in Reaxys 233/1037 Yield

Conditions & References With methanol, Time= 7h, T= 60 °C , solvolysis, Product distribution, Further Variations: Reagents Fujita, Morifumi; Sakanishi, Yuichi; Okuyama, Tadashi; Journal of the American Chemical Society; vol. 122; nb. 36; (2000); p. 8787 - 8788 View in Reaxys

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(v4)

H (v5) C –(v5)

FK (v4)

(v5) (v5) (v5)

H (v5) C – (v5)

(v4)

(v5)(v5)

(v5) Fe 2+ (v5) (v10)

CH –

Sn Sn

(v10)

–HC

CH –

(v5)

Fe 2+

(v4)

(v5)

(v5)(v5)

(v5)

Fe 2+

(v4)

HC (v5) (v5) (v5)

(v5) (v5)

(v5)

(v10)

–

(v4)

(v5) (v5) (v5)

Sn Sn F F

(v5)

CH –

(v10)

CH –

(v4)

(v5) (v5)

(v4)

Fe 2+

(v5)

Rx-ID: 27140617 View in Reaxys 234/1037 Yield

Conditions & References

89 %

in diethyl ether, dichloromethane, water, under N2 atm. I2 was added to soln. (FcMe2SiCH2SnPh2)2CH2 in CH2Cl2, react. mixt. was stirred overnight, solvent and PhI were emoved in vacuo, residue was dissolved in Et2O, KF in water was added and mixt. was stirred for 3 d; org. layer was separated, dried over Na2SO4, Et2O was evapd.; elem. anal. Altmann, Reiner; Gausset, Olivier; Horn, Dagmar; Jurkschat, Klaus; Schuermann, Markus; et al.; Organometallics; vol. 19; (2000); p. 430 - 443 ; (from Gmelin) View in Reaxys

(v5)

CH –

(v4)

Fe 2+

(v10)

(v5)

– (v5) C Si (v4) (v5)

(v5)

Sn F

(v5)

(v5) (v5)

(v5)

CH –

(v4)

Fe 2+ F Sn – (v5) C Si (v4) (v5)

Rx-ID: 27140618 View in Reaxys 235/1037 Yield

Conditions & References

98 %

in pyridine, diethyl ether, water, under N2 atm. I2 was added to soln. fc(SiMe2CH2SnPh3)2 in CH2Cl2 and stirred overnight, solvent and iodobenzene were removed in vacuo, residue was dissolved in Et2O and added to soln. KF in water, suspn. was stirredovernight; ppt. was filtered, washed with water and Et2O; elem. anal. Altmann, Reiner; Gausset, Olivier; Horn, Dagmar; Jurkschat, Klaus; Schuermann, Markus; et al.; Organometallics; vol. 19; (2000); p. 430 - 443 ; (from Gmelin) View in Reaxys

(v4)

H (v5) C –(v5) Si

Fe 2+ (v4)

–

(v10)

(v5)

(v5)(v5)

CH –

(v5)

Sn Sn

(v4)

(v5)

Fe 2+ (v5) (v10)

CH –

(v5) (v5) (v5) (v5)

(v5)

AgCl

(v4)

(v5) (v5)

(v4)

H (v5) C – (v5)

(v5)(v5)

Fe 2+ (v4)

–HC

Si (v10)

(v5) (v5) (v5)(v5)

(v5) (v5) (v5)

Sn Cl Sn Cl

(v5)

CH –

Fe 2+ (v10)

(v4)

AgI

CH –

(v4)

(v5) (v5)

Rx-ID: 27140620 View in Reaxys 236/1037 Yield 89 %

Conditions & References in dichloromethane, acetonitrile, under N2 atm. I2 was added to soln. (FcMe2SiCH2SnPh2)2CH2 in CH2Cl2, react. mixt. was stirred overnight, solvent and PhI were emoved in vacuo, residue was dissolved in CH3CN/CH2Cl2, AgCl was added under exclusion oflight and mixt. was stirred for 14 d; ppt. was filtered off, solvent was removed in vacuo; elem. anal. Altmann, Reiner; Gausset, Olivier; Horn, Dagmar; Jurkschat, Klaus; Schuermann, Markus; et al.; Organometallics; vol. 19; (2000); p. 430 - 443 ; (from Gmelin) View in Reaxys

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(v5)

CH –

(v4)

Fe 2+

(v10)

AgCl

(v10)

(v5)

(v5) (v5)

(v5)

CH –

(v4)

AgI

Fe 2+ Cl Sn

(v5)

– (v5) C Si (v4) (v5)

(v5)

Sn Cl

(v5)

– (v5) C Si (v4) (v5)

Rx-ID: 27140621 View in Reaxys 237/1037 Yield

Conditions & References

96 %

in pyridine, acetonitrile, under N2 atm. I2 was added to soln. fc(SiMe2CH2SnPh3)2 in CH2Cl2 and stirred overnight, solvent and iodobenzene were removed in vacuo, residue was dissolved in CH3CN/CH2Cl, AgCl was added under exclusion of light and mixt. was stirred for 11 days; ppt. was filtered off, solvent was removed in vacuo; elem. anal. Altmann, Reiner; Gausset, Olivier; Horn, Dagmar; Jurkschat, Klaus; Schuermann, Markus; et al.; Organometallics; vol. 19; (2000); p. 430 - 443 ; (from Gmelin) View in Reaxys

(v4)

H (v5) Sn – (v5) C (v5) (v5) (v5) (v5) Si Si CH –

(v5)

Fe 2+ (v5)

(v10)

–HC (v4)

(v5) (v5)

(v5) (v5) (v5) (v5)

(v10)

CH –

Si Sn

I H (v5) Sn – (v5) C(v5) (v5)(v5) (v5) Si Si CH –

(v4)

Fe 2+

(v5)

Fe 2+

(v5)

(v10)

–HC (v4)

(v4)

(v5) (v5)

Fe 2+ Si

Sn I

(v4)

(v5)

(v10)

CH –

(v5) (v5) (v5) (v5)

(v4)

Rx-ID: 27140640 View in Reaxys 238/1037 Yield

Conditions & References

99 %

in dichloromethane, under N2atm. i2 was added to soln. fc(SiMe2CH2SnPh2CH2SiMe2)2fc in CH2Cl2, react. mixt. was stirred overnight; solvent and iodobenzene were removed in vacuo, residue was recrystd. from hexane; elem. anal. Altmann, Reiner; Gausset, Olivier; Horn, Dagmar; Jurkschat, Klaus; Schuermann, Markus; et al.; Organometallics; vol. 19; (2000); p. 430 - 443 ; (from Gmelin) View in Reaxys

(v1)3+ Tl (v1) F–

C–

(v4)

(v1)

(v4)

–F

B3+ F–F–

ITl

(v1) (v1)

Rx-ID: 27151625 View in Reaxys 239/1037 Yield

Conditions & References in methanol, water, byproducts: KBF4; aq. KI added to a soln. of Tl deriv. in MeOH; yellow ppt. of TlI formed immediately; mixt. stirred for 10 min at room temp. and then for 20 minwith heating; ppt. filtered off, washed with water and MeOH Gun'kin; Pankst'yanov; Popova; Kleimenova; Russian Journal of General Chemistry; vol. 70; nb. 1; (2000); p. 37 - 39 ; (from Gmelin) View in Reaxys -1

(v4)

B FF

I+

O O

Rx-ID: 4685669 View in Reaxys 240/1037

94/330

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Yield

Conditions & References Time= 168h, T= 70 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Okuyama; Ochiai; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4785 - 4786 View in Reaxys Time= 168h, T= 70 °C , Product distribution, Mechanism Okuyama; Ochiai; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4785 - 4786 View in Reaxys

7 % Chromat.

Time= 168h, T= 70 °C , Product distribution, Rate constant, Mechanism Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1 F (v4)

B FF

O I+

Rx-ID: 4867169 View in Reaxys 241/1037 Yield

Conditions & References

82 %, 30 % Chromat.

82 %, 30 % Spectr.

With chromium dichloride, nickel dichloride in N,N-dimethyl-formamide, Time= 5h, T= 25 °C , Arylation Chen, Da-Wei; Ochiai, Masahito; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6804 - 6814 View in Reaxys

-1 F (v4)

B FF

I I+

Rx-ID: 4878224 View in Reaxys 242/1037 Yield 78 %, 34 % Chromat.

Conditions & References With chromium dichloride, nickel dichloride in N,N-dimethyl-formamide, Time= 5h, Ambient temperature Chen, Da-Wei; Takai, Kazuhiko; Ochiai, Masahito; Tetrahedron Letters; vol. 38; nb. 47; (1997); p. 8211 - 8214 View in Reaxys

78 %, 34 % Spectr.

95/330

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-1 F (v4)

B FF

I+

Rx-ID: 4878803 View in Reaxys 243/1037 Yield

Conditions & References

82 %, 42 % Chromat.

82 %, 42 % Spectr.

-1 F (v4)

B FF

I I+

Rx-ID: 4881203 View in Reaxys 244/1037 Yield 92 %

Conditions & References With chromium dichloride, nickel dichloride in N,N-dimethyl-formamide, Time= 5h, T= 25 °C , Arylation, Product distribution, Further Variations: Temperatures, various reaction times, amounts of reagents Chen, Da-Wei; Ochiai, Masahito; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6804 - 6814 View in Reaxys

87 %, 44 % Chromat.

With chromium dichloride, nickel dichloride in N,N-dimethyl-formamide, Time= 5h, Ambient temperature Chen, Da-Wei; Takai, Kazuhiko; Ochiai, Masahito; Tetrahedron Letters; vol. 38; nb. 47; (1997); p. 8211 - 8214 View in Reaxys With chromium dichloride, nickel dichloride in N,N-dimethyl-formamide, Time= 5h, Ambient temperature, var. of aldehydes, Mechanism Chen, Da-Wei; Takai, Kazuhiko; Ochiai, Masahito; Tetrahedron Letters; vol. 38; nb. 47; (1997); p. 8211 - 8214 View in Reaxys -1 F (v4)

B FF

I+

Rx-ID: 5135851 View in Reaxys 245/1037 Yield 0.60 % Chromat., 0.79 % Chromat., 26 % Chromat.

Conditions & References Time= 50h, T= 50 °C , effect of additives; rate const. at 60 deg C, Product distribution, Rate constant, Mechanism Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys

96/330

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-1 F (v4)

B FF

I+ 2H

O 2H

Rx-ID: 5135896 View in Reaxys 246/1037 Yield

Conditions & References Time= 50h, T= 50 °C , Product distribution Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1 F (v4)

B FF

I+

O 2H

Rx-ID: 5135897 View in Reaxys 247/1037 Yield

Conditions & References With tetrabutylammomium bromide, Time= 25h, T= 50 °C , Product distribution Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1 F (v4)

B FF

I I+

Rx-ID: 5140917 View in Reaxys 248/1037 Yield

Conditions & References

1.8 % Chromat., 1.1 % Chromat., 27 % Chromat.

With trifluoroacetic acid, Time= 50h, T= 60 °C , effect of additives; rate const. at 60 deg C, Product distribution, Rate constant, Mechanism Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1

F HO

(v4)

F O

B FF

F F

O F

I+

O F F F

Rx-ID: 5141804 View in Reaxys 249/1037

97/330

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Yield

Conditions & References Time= 240h, T= 50 °C , rate const. at 60 deg C; effect of water studied, Product distribution, Rate constant, Mechanism Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1

(v4)

B FF

I+

O O

F F F

Rx-ID: 5141805 View in Reaxys 250/1037 Yield

Conditions & References Time= 240h, T= 50 °C , Product distribution Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys O

Rx-ID: 5143609 View in Reaxys 251/1037 Yield

Conditions & References With iodosylbenzene, (salen)MnIII in acetonitrile, T= 25 °C , oxidation of aryl methyl sulfoxides by generated in situ oxo(salen)manganese(V)complexes; effect of complex substituent on the reaction rate; reactivity-selectivity principle; effect of adding trichloroacetic acid, Rate constant

79 %

Chellamani, Arunachalam; Kulanthaipandi, Periasamy; Rajagopal, Seenivasan; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2232 - 2239 View in Reaxys -1 F (v4)

B FF

I I+

Rx-ID: 5151547 View in Reaxys 252/1037 Yield

Conditions & References With sodium acetate in methanol, Time= 4h, T= 50 °C , Product distribution Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1 F

(v4)

B FF

I+

98/330

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O 2H

Rx-ID: 5153829 View in Reaxys 253/1037 Yield

Conditions & References Time= 168h, T= 70 °C , Product distribution Okuyama, Tadashi; Ishida, Yoshimi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 2; (1999); p. 163 - 170 View in Reaxys -1

F (v4)

B FF

Rx-ID: 5178148 View in Reaxys 254/1037 Yield

Conditions & References

50 %, 3.4 %, 21 %

in acetic acid, Time= 40h, T= 60 °C , Solvolysis, Further byproducts given Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys

30 % Chromat., 8.9 % Chromat., 15 % Chromat.

With 2,2,2-trifluoroethanol, Time= 30h, T= 60 °C , Further byproducts given Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 View in Reaxys

I+

Cl –

Rx-ID: 5192938 View in Reaxys 255/1037 Yield

Conditions & References

70 %

With bis-triphenylphosphine-palladium(II) chloride, potassium hydroxide, Time= 1h, T= 50 °C , Carbonylation Xia, Min; Chen, Zhen-Chu; Journal of Chemical Research - Part S; nb. 5; (1999); p. 328 - 329 View in Reaxys

I+

Cl –O

S O

99/330

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I O

Rx-ID: 5192939 View in Reaxys 256/1037 Yield

Conditions & References

61 %

I+

Br–

Rx-ID: 5192940 View in Reaxys 257/1037 Yield

Conditions & References

67 %

I+

Br–

O HO

Rx-ID: 5192943 View in Reaxys 258/1037 Yield

Conditions & References

77 %

Cl –O

I OH

Cl O S

Rx-ID: 5192953 View in Reaxys 259/1037 Yield

Conditions & References

54 %

N+

S O O

Rx-ID: 5222382 View in Reaxys 260/1037 Yield

Conditions & References With tetra-(n-butyl)ammonium iodide in acetonitrile, Time= 0.75h, T= 20 °C , Substitution Barbero; Degani; Dughera; Fochi; Journal of Organic Chemistry; vol. 64; nb. 10; (1999); p. 3448 - 3453

100/330

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View in Reaxys With tetra-(n-butyl)ammonium iodide in acetonitrile, Time= 0.75h, T= 20 °C , Substitution, Product distribution, Further Variations: various reagent ratios Barbero; Degani; Dughera; Fochi; Journal of Organic Chemistry; vol. 64; nb. 10; (1999); p. 3448 - 3453 View in Reaxys -1 F

(v4)

B FF

I+

Rx-ID: 5276151 View in Reaxys 261/1037 Yield

Conditions & References

56 %

With chromium dichloride in N,N-dimethyl-formamide, Time= 5h, T= 25 °C , Arylation, Product distribution Chen, Da-Wei; Ochiai, Masahito; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6804 - 6814 View in Reaxys

Rx-ID: 5291858 View in Reaxys 262/1037 Yield

Conditions & References With chromium dichloride in N,N-dimethyl-formamide, T= 25 °C , Decomposition, Kinetics Chen, Da-Wei; Ochiai, Masahito; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6804 - 6814 View in Reaxys

Rx-ID: 5292106 View in Reaxys 263/1037 Yield

I C

Rx-ID: 5292114 View in Reaxys 264/1037 Yield

101/330

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-1 F (v4)

B FF

I+

Rx-ID: 5315144 View in Reaxys 265/1037 Yield

Conditions & References T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1 F (v4)

B FF

I+

Rx-ID: 5315145 View in Reaxys 266/1037 Yield

Conditions & References With sodium acetate, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1 F (v4)

B FF

Rx-ID: 5315147 View in Reaxys 267/1037 Yield

Conditions & References

25 %, 12 %, With sodium acetate, Time= 16h, T= 60 °C , Solvolysis, Further byproducts given 22 % Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys

102/330

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T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1 F (v4)

B FF

F OH

I+

Rx-ID: 5319793 View in Reaxys 268/1037 Yield

B FF

Rx-ID: 5319795 View in Reaxys 269/1037 Yield

Rx-ID: 5321991 View in Reaxys 270/1037 Yield

Conditions & References With M2PtCl4 in N,N-dimethyl-formamide, T= 80 °C , Substitution, oxidative coupling, Kinetics, Further Variations: effect of LiCl Bezbozhnaya; Litvinenko; Skripnik; Zamashchikov; Russian Journal of General Chemistry; vol. 69; nb. 8; (1999); p. 1198 1203 View in Reaxys

103/330

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-1 F (v4)

B FF

I+

Rx-ID: 5342062 View in Reaxys 271/1037 Yield

Conditions & References

34 %, 15 %, in 2-methoxy-ethanol, Time= 15h, T= 60 °C , Solvolysis, Further byproducts given 7.8 % Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1 F (v4)

B FF

I+

Rx-ID: 5342063 View in Reaxys 272/1037 Yield

Conditions & References

34 %, 177 %, 11 %

in 2,2,2-trifluoroethanol, Time= 80h, T= 60 °C , Solvolysis, Further byproducts given Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys

-1 F (v4)

B FF

I+

Rx-ID: 5342064 View in Reaxys 273/1037 Yield

Conditions & References

62 %, 11 %, in ethanol, Time= 40h, T= 60 °C , Solvolysis, Further byproducts given 51 % Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys

104/330

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-1 F (v4)

B FF

I+

Rx-ID: 5342065 View in Reaxys 274/1037 Yield

Conditions & References in 2,2,2-trifluoroethanol, water, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1

F (v4)

B FF

I+

Rx-ID: 5342066 View in Reaxys 275/1037 Yield

Conditions & References in water, T= 60 °C , Hydrolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1

F (v4)

B FF

Rx-ID: 5342074 View in Reaxys 276/1037 Yield 50 %, 2.7 %, 21 %

Conditions & References in acetic acid, Time= 40h, T= 60 °C , Solvolysis, Further byproducts given Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769

105/330

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View in Reaxys -1 F (v4)

B FF

Rx-ID: 5342075 View in Reaxys 277/1037 Yield

F (v4)

B FF

Rx-ID: 5342076 View in Reaxys 278/1037 Yield

Conditions & References in ethanol, water, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1

F (v4)

B FF

106/330

2018-06-17 20:31:40

Rx-ID: 5342077 View in Reaxys 279/1037 Yield

Conditions & References in ethanol, 2,2,2-trifluoroethanol, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys in 2,2,2-trifluoroethanol, water, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1

F (v4)

B FF

Rx-ID: 5342078 View in Reaxys 280/1037 Yield

Conditions & References With sodium acetate in methanol, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769 View in Reaxys -1

F (v4)

B FF

Rx-ID: 5342079 View in Reaxys 281/1037 Yield

Conditions & References in 2-methoxy-ethanol, T= 60 °C , Solvolysis, Kinetics Okuyama, Tadashi; Yamataka, Hiroshi; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 72; nb. 12; (1999); p. 2761 - 2769

107/330

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View in Reaxys

Rx-ID: 26083318 View in Reaxys 282/1037 Yield

Conditions & References in 1,4-dioxane, Kinetics, in darkness, 20-45°C; products not isolated, reaction monitoring by spectrophotometry Gun'kin; Butin; Russian Chemical Bulletin; vol. 48; nb. 3; (1999); p. 448 - 452 ; (from Gmelin) View in Reaxys O O Tl

I O

Rx-ID: 26083387 View in Reaxys 283/1037 Yield

I Tl

O O

Rx-ID: 26083388 View in Reaxys 284/1037 Yield

Rx-ID: 26083395 View in Reaxys 285/1037 Yield

108/330

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-1 F (v4)

B FF

I+

I Cl

Rx-ID: 2746498 View in Reaxys 286/1037 Yield

Conditions & References

4.9 %, 95 % With tetrabutyl-ammonium chloride in tetrahydrofuran, Time= 0.5h, T= 25 °C , Substitution, elimination Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Oshima, Kunio; Imamura, Shohei; Yamataka, Hiroshi; Asano, Tsutomu; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 243 - 257 View in Reaxys With tetrabutyl-ammonium chloride, tetrabutylammonium perchlorate in acetonitrile, T= 25 °C Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Ochiai, Masahito; Journal of the American Chemical Society; vol. 120; nb. 10; (1998); p. 2275 - 2282 View in Reaxys 14 % Chromat., 83 % Chromat.

With tetrabutyl-ammonium chloride in dichloromethane, Time= 10h, Ambient temperature, other also deuterated (E)-δ-alkylvinyliodonium tetrafluoroborates, var. reagents, solvents and time; stereoselectivity, Product distribution Ochiai, Masahito; Oshima, Kunio; Masaki, Yukio; Journal of the American Chemical Society; vol. 113; nb. 18; (1991); p. 7059 - 7061 View in Reaxys With tetrabutyl-ammonium chloride, tetrabutylammonium perchlorate in acetonitrile, T= 25 °C , var. solvents and var. concentration of reagents, Rate constant Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Ochiai, Masahito; Journal of the American Chemical Society; vol. 120; nb. 10; (1998); p. 2275 - 2282 View in Reaxys With tetrabutyl-ammonium chloride in chloroform, T= 25 °C , Substitution, elimination, Kinetics, Further Variations: Reagents, Solvents, Pressures Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Oshima, Kunio; Imamura, Shohei; Yamataka, Hiroshi; Asano, Tsutomu; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 243 - 257 View in Reaxys

Rx-ID: 3918655 View in Reaxys 287/1037 Yield 1.5 %, 8.7 %

Conditions & References With iodine pentoxide, sulfuric acid, iodine in acetic acid, Time= 40h, T= 60 °C Brazdil, Linda C.; Cutler, Carlo J.; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9621 - 9622 View in Reaxys

8.6 %, 46 % With iodine pentoxide, sulfuric acid, iodine in acetic acid, Time= 24h Brazdil, Linda C.; Fitch, Jill L.; Cutler, Carlo J.; Haynik, Denise M.; Ace, Eryn R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (1998); p. 933 - 936 View in Reaxys 8 %, 46 %

With iodine pentoxide, sulfuric acid, iodine in acetic acid, Time= 40h, T= 60 °C Brazdil, Linda C.; Cutler, Carlo J.; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9621 - 9622

109/330

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View in Reaxys 8.0 %, 46 % With iodine pentoxide, sulfuric acid, iodine in acetic acid, Time= 40h, T= 60 °C Brazdil, Linda C.; Cutler, Carlo J.; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9621 - 9622 View in Reaxys 30 %, 40 %

With iodine, fluorine in chloroform, trichlorofluoromethane, Time= 5h, T= 25 °C Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys With iodine, fluorine in chloroform, trichlorofluoromethane, Time= 5h, T= 25 °C , other aromatic compounds Rozen, Shlomo; Zamir, Dov; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3552 - 3555 View in Reaxys

0.01 g, 0.13 g

With sodium vanadate, air, trifluorormethanesulfonic acid, iodine, Time= 1.5h, T= 100 °C , p= 7355.08Torr , other metal salt and oxides as catalyst (Fe(2+), Fe(3+), Cu(2+), V(3+), V(5+), Ti(4+), Zr(4+), Ni(2+), Pd(2+), Zn(2+), Cd(2+) Ag(1+), Tl(1+), Mn(4+), Sb(3+)), pressure from 2 to 10 kg/cm2, reaction time from 1.5 to 9 h, CF3CO2H, CH3SO3H as solvents, Product distribution Shimizu, Atsushi; Yamataka, Kazunori; Isoya, Toshiro; Bulletin of the Chemical Society of Japan; vol. 58; nb. 5; (1985); p. 1611 - 1612 View in Reaxys With iodine pentoxide, sulfuric acid, iodine in acetic acid, T= 323 - 343 °C , influence of I2, H2SO4 conc., Kinetics Brazdil, Linda C.; Fitch, Jill L.; Cutler, Carlo J.; Haynik, Denise M.; Ace, Eryn R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (1998); p. 933 - 936 View in Reaxys

0.01 g, 0.13 g

With sodium vanadate, air, trifluorormethanesulfonic acid, iodine, Time= 1.5h, T= 100 °C , p= 7355.08Torr Shimizu, Atsushi; Yamataka, Kazunori; Isoya, Toshiro; Bulletin of the Chemical Society of Japan; vol. 58; nb. 5; (1985); p. 1611 - 1612 View in Reaxys

O B O

Rx-ID: 4817959 View in Reaxys 288/1037 Yield

Conditions & References With N-iodo-succinimide in acetonitrile, T= 81 °C Thiebes, Christoph; Prakash, G. K. Surya; Petasis, Nicos A.; Olah, George A.; Synlett; nb. 2; (1998); p. 141 - 142 View in Reaxys -1

F (v4)

B FF

Rx-ID: 4848877 View in Reaxys 289/1037 Yield

Conditions & References With tetrabutyl-ammonium chloride, tetrabutylammonium perchlorate in acetonitrile, T= 25 °C , var. solvents and var. concentration of reagents, Rate constant, Mechanism

110/330

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Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Ochiai, Masahito; Journal of the American Chemical Society; vol. 120; nb. 10; (1998); p. 2275 - 2282 View in Reaxys -1 F (v4)

B FF

I Cl

Rx-ID: 4849065 View in Reaxys 290/1037 Yield

Conditions & References With tetrabutyl-ammonium chloride, tetrabutylammonium perchlorate in acetonitrile, T= 25 °C , var. solvents and var. concentration of reagents, Rate constant Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Ochiai, Masahito; Journal of the American Chemical Society; vol. 120; nb. 10; (1998); p. 2275 - 2282 View in Reaxys -1

F (v4)

B FF

I +I

Rx-ID: 4853267 View in Reaxys 291/1037 Yield

F (v4)

B FF

I Cl

I+

Rx-ID: 5002371 View in Reaxys 292/1037 Yield

Conditions & References With tetrabutyl-ammonium chloride in acetonitrile, T= 50 °C , Rate constant, Mechanism Okuyama, Tadashi; Oka, Hsjime; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 8; (1998); p. 1915 - 1921 View in Reaxys -1

F (v4)

B FF

I I+

Rx-ID: 5002372 View in Reaxys 293/1037 Yield

Conditions & References With tetrabutylammomium bromide in acetonitrile, T= 50 °C , Rate constant, Mechanism Okuyama, Tadashi; Oka, Hsjime; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 8; (1998); p. 1915 - 1921

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View in Reaxys -1 F (v4)

B FF

I+

I Br

Rx-ID: 5002373 View in Reaxys 294/1037 Yield

Conditions & References With 2,2,2-trifluoroethanol, tetrabutylammomium bromide in acetonitrile, T= 50 °C , Product distribution Okuyama, Tadashi; Oka, Hsjime; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 8; (1998); p. 1915 - 1921 View in Reaxys -1

F (v4)

B FF

I I

I+

Rx-ID: 5002374 View in Reaxys 295/1037 Yield

Conditions & References With tetra-(n-butyl)ammonium iodide in acetonitrile, T= 50 °C , Rate constant, Mechanism Okuyama, Tadashi; Oka, Hsjime; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 8; (1998); p. 1915 - 1921 View in Reaxys I O

I O

Rx-ID: 5021032 View in Reaxys 296/1037 Yield

Conditions & References in dichloromethane-d2, T= -15 °C Berger, Christian; Dieterich, Stefan; Dilger, Ulrich; Geuenich, Daniel; Helios, Heike; Herges, Rainer; Kirchmer, Peter; Roettele, Herbert; Schroeder, Gerhard; Angewandte Chemie - International Edition; vol. 37; nb. 13-14; (1998); p. 1854 1857 View in Reaxys in dichloromethane-d2, T= -15 °C , half-life; ΔG(excit.), ΔH(excit.), ΔS(excit.); further temperatures, Thermodynamic data Berger, Christian; Dieterich, Stefan; Dilger, Ulrich; Geuenich, Daniel; Helios, Heike; Herges, Rainer; Kirchmer, Peter; Roettele, Herbert; Schroeder, Gerhard; Angewandte Chemie - International Edition; vol. 37; nb. 13-14; (1998); p. 1854 1857 View in Reaxys -1

F (v4)

B FF

I+

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Rx-ID: 5036143 View in Reaxys 297/1037 Yield

Conditions & References With tetrabutylammomium bromide in acetonitrile, T= 50 °C , Rate constant, Mechanism, Product distribution Okuyama, Tadashi; Oka, Hsjime; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 8; (1998); p. 1915 - 1921 View in Reaxys I

I -1 I+

F F

F (v6)

P F

Rx-ID: 5045784 View in Reaxys 298/1037 Yield

Conditions & References With 4-methylbenzenediazonium hexafluorophosphate in acetonitrile, Time= 6.5h, T= 15 °C , Irradiation, various arenediazonium salts, Product distribution, Mechanism Geahigan, Karen B.; Taintor, Richard J.; George, Bindu M.; Meagher, Denise A.; Nalli, Thomas W.; Journal of Organic Chemistry; vol. 63; nb. 18; (1998); p. 6141 - 6145 View in Reaxys

Rx-ID: 5049517 View in Reaxys 299/1037 Yield

Conditions & References With iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. in dichloromethane, iron 5-(pentafluorophenyl)-10,15,20tris(2,6-dichlorophenyl)porphyrin was used as catalyst, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys With iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. in dichloromethane, iron 5-(pentafluorophenyl)-10,15,20tris(2,6-dichlorophenyl)porphyrin fixed on silica was used as catalyst, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys With iron 5,10,15,20-tetrakis-(2',6'-dichlorophenyl)porphyrinate in dichloromethane, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys With [FeIII(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinate)] in dichloromethane, Oxidation

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Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys

I O

Rx-ID: 5051406 View in Reaxys 300/1037 Yield 100 %

100 %

With [FeIII(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinate)] in dichloromethane, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys

54 %

With iron 5,10,15,20-tetrakis-(2',6'-dichlorophenyl)porphyrinate in dichloromethane, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys

33 %

With iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. in dichloromethane, iron 5-(pentafluorophenyl)-10,15,20tris(2,6-dichlorophenyl)porphyrin fixed on silica was used as catalyst, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys

I O

Rx-ID: 5051407 View in Reaxys 301/1037 Yield 100 %

Conditions & References With [FeIII(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinate)] in dichloromethane, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys

96 %

60 %

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60 %

With iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. in dichloromethane, iron 5-(pentafluorophenyl)-10,15,20tris(2,6-dichlorophenyl)porphyrin was used as catalyst, Oxidation Assis, Marilda Das Dores; Lindsay Smith, John R.; Journal of the Chemical Society. Perkin Transactions 2; nb. 10; (1998); p. 2221 - 2226 View in Reaxys O

Rx-ID: 5053120 View in Reaxys 302/1037 Yield 48 %

42 %

32 %

H I

Rx-ID: 5053577 View in Reaxys 303/1037 Yield 81 %

69 %

56 %

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52 %

F (v4)

B FF

I I+

Rx-ID: 5060254 View in Reaxys 304/1037 Yield

Conditions & References

94 %

With tetrabutyl ammonium fluoride in dichloromethane, Time= 10h, T= 20 °C , Elimination Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Oshima, Kunio; Imamura, Shohei; Yamataka, Hiroshi; Asano, Tsutomu; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 243 - 257 View in Reaxys -1

F (v4)

B FF

I+

I Br

Rx-ID: 5060255 View in Reaxys 305/1037 Yield

Conditions & References

6.7 %, 74 % With tetrabutylammomium bromide in chloroform, Time= 1.5h, T= 25 °C , Substitution, elimination Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Oshima, Kunio; Imamura, Shohei; Yamataka, Hiroshi; Asano, Tsutomu; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 243 - 257 View in Reaxys -1 F (v4)

B FF

I+

Rx-ID: 5060257 View in Reaxys 306/1037 Yield

Conditions & References

3.5 %

With tetrabutyl-ammonium chloride in trifluoroacetic acid, Time= 50h, T= 50 °C , Substitution, elimination Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Oshima, Kunio; Imamura, Shohei; Yamataka, Hiroshi; Asano, Tsutomu; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 243 - 257 View in Reaxys -1

F (v4)

B FF

I+

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Rx-ID: 5060258 View in Reaxys 307/1037 Yield 0.6 %, 85 %, 15 %

Conditions & References With tetrabutylammomium bromide in trifluoroacetic acid, Time= 25h, T= 50 °C , Substitution, elimination Okuyama, Tadashi; Takino, Tomoki; Sato, Koichi; Oshima, Kunio; Imamura, Shohei; Yamataka, Hiroshi; Asano, Tsutomu; Ochiai, Masahito; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 243 - 257 View in Reaxys O

Rx-ID: 5081572 View in Reaxys 308/1037 Yield

B FF

I+

Rx-ID: 5136190 View in Reaxys 309/1037 Yield

Conditions & References

1.7 % Chro- With sodium acetate, Time= 1h, T= 60 °C mat., 9.3 % Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 Chromat., 80 % Chro- View in Reaxys mat.

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-1 F (v4)

B FF

Rx-ID: 5136191 View in Reaxys 310/1037 Yield

Conditions & References

F HO

B FF

I+

F O

Rx-ID: 5141816 View in Reaxys 311/1037 Yield

Conditions & References

34 % Chro- Time= 80h, T= 60 °C , Further byproducts given mat., 17 % Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 Chromat., 2.9 % Chro- View in Reaxys mat. -1 F (v4)

B FF

OH I+

Rx-ID: 5153874 View in Reaxys 312/1037 Yield 47 % Chromat., 22 % Chromat.,

Conditions & References Time= 80h, T= 60 °C , Further byproducts given Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 View in Reaxys

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9.0 % Chromat. -1 F (v4)

B FF

I+

Rx-ID: 5178144 View in Reaxys 313/1037 Yield

Conditions & References

50 % Chromat., 2.7 % Chromat., 21 % Chromat.

With acetic acid, Time= 40h, T= 60 °C , Further byproducts given Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 View in Reaxys

-1 F (v4)

B FF

I+

Rx-ID: 5178145 View in Reaxys 314/1037 Yield

Conditions & References

5.4 % Chro- With methanol, Time= 46h, T= 60 °C , Further byproducts given mat., 2.7 % Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 Chromat., 61 % Chro- View in Reaxys mat. -1 F (v4)

B FF

Rx-ID: 5178146 View in Reaxys 315/1037

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Yield

Conditions & References

50 % Chro- With acetic acid, Time= 40h, T= 60 °C , variation of reagent; also with Z-isomer, Mechanism mat., 2.0 % Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 Chromat., 2.7 % Chro- View in Reaxys mat., 3.4 % Chromat., 21 % Chromat. -1 F (v4)

B FF

Rx-ID: 5178147 View in Reaxys 316/1037 Yield

Conditions & References

25 % Chromat., 7.0 % Chromat., 26 % Chromat.

With methanol, Time= 80h, T= 60 °C , Further byproducts given Okuyama, Tadashi; Sato, Koichi; Ochiai, Masahito; Chemistry Letters; nb. 11; (1998); p. 1177 - 1178 View in Reaxys

O–

O S

O F

O O–

F O

N+

Rx-ID: 4664045 View in Reaxys 317/1037 Yield

Conditions & References

78 %

in dichloromethane, Time= 0.166667h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys

O–

O S

O F

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O O–

F O

N+

Rx-ID: 4664046 View in Reaxys 318/1037 Yield

Conditions & References

85 %

in dichloromethane, Time= 0.166667h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys +I

O–

O S

O O

I S

Rx-ID: 4668819 View in Reaxys 319/1037 Yield

Conditions & References

95 % Spectr.

With potassium fluoride in dichloromethane, Time= 72h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys -1 F (v4)

B FF

O O

Rx-ID: 4674547 View in Reaxys 320/1037 Yield 25 %, 8 %, 19 %

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 1h, Ambient temperature, Further byproducts given Ochiai, Masahito; Shu, Toshifusa; Nagaoka, Takema; Kitagawa, Yutaka; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2130 - 2138 View in Reaxys

25 %, 8 %, 19 %

With potassium tert-butylate in tetrahydrofuran, Time= 1h, Ambient temperature, Further byproducts given Ochiai, Masahito; Shu, Toshifusa; Nagaoka, Takema; Kitagawa, Yutaka; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2130 - 2138

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View in Reaxys -1 F (v4)

B FF

I O O

O I

Rx-ID: 4674548 View in Reaxys 321/1037 Yield

Conditions & References

39 %, 25 %, With potassium tert-butylate in tetrahydrofuran, Time= 1h, Ambient temperature, in the presence or absence of various radical 8 %, 19 %, inhibitors, different iodonium salts, Product distribution, Mechanism 45 % Ochiai, Masahito; Shu, Toshifusa; Nagaoka, Takema; Kitagawa, Yutaka; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2130 - 2138 View in Reaxys

–S

O–

O S

Li+ F

O O

F O

O S S

Rx-ID: 4679291 View in Reaxys 322/1037 Yield 90 % Spectr.

Conditions & References in dichloromethane, Time= 3h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys

–S

O–

O S

Li+

O O

F O

O S S

Rx-ID: 4679292 View in Reaxys 323/1037 Yield 80 % Spectr.

Conditions & References in dichloromethane, Time= 3h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys

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O–

O S

O O

O N+

O–

O S

I F

Rx-ID: 4686880 View in Reaxys 324/1037 Yield

Conditions & References

61 % Spectr.

in dichloromethane, Time= 0.5h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys +

O–

O S

O O

O O S

O– F

N+

I F

O F

Rx-ID: 4686881 View in Reaxys 325/1037 Yield

Conditions & References

95 % Spectr.

in dichloromethane, Time= 0.333333h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys

O–

O S

O O

O– F

O S

I F

P+ O

S O O

Rx-ID: 4691352 View in Reaxys 326/1037 Yield 82 % Spectr.

Conditions & References in dichloromethane, Time= 2h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys

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O–

O S

O O

O–

O S

I F

P+ O

Rx-ID: 4691353 View in Reaxys 327/1037 Yield

Conditions & References

85 % Spectr.

in dichloromethane, Time= 2h, Ambient temperature Zhdankin; Erickson; Hanson; Journal of the American Chemical Society; vol. 119; nb. 20; (1997); p. 4775 - 4776 View in Reaxys

O–

I+

F O

I O

Rx-ID: 4788606 View in Reaxys 328/1037 Yield

Conditions & References

35 %, 25 %

in methanol, Time= 16h, Ambient temperature, Further byproducts given Hinkle, Robert J.; Thomas, David B.; Journal of Organic Chemistry; vol. 62; nb. 22; (1997); p. 7534 - 7535 View in Reaxys

O–

F F

Rx-ID: 4788607 View in Reaxys 329/1037 Yield 51 %

Conditions & References in chloroform-d1, Time= 16h, Ambient temperature, Product distribution Hinkle, Robert J.; Thomas, David B.; Journal of Organic Chemistry; vol. 62; nb. 22; (1997); p. 7534 - 7535 View in Reaxys

51 %

in chloroform-d1, Time= 16h, Ambient temperature Hinkle, Robert J.; Thomas, David B.; Journal of Organic Chemistry; vol. 62; nb. 22; (1997); p. 7534 - 7535

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View in Reaxys O O

Cl O

I O

Cl O

O O

Rx-ID: 4860984 View in Reaxys 330/1037 Yield

Conditions & References in dichloromethane, acetonitrile, Ambient temperature, other alkenes, reaction time 3-4 h, Mechanism De Mico, Antonella; Margarita, Roberto; Parlanti, Luca; Piancatelli, Giovanni; Vescovi, Andrea; Tetrahedron; vol. 53; nb. 49; (1997); p. 16877 - 16882 View in Reaxys

O Br

Rx-ID: 4870509 View in Reaxys 331/1037 Yield

Conditions & References With trimethylsilyl bromide, [bis(acetoxy)iodo]benzene, Time= 0.0833333h, other substrate, Mechanism Evans, P. Andrew; Brandt, Thomas A.; Journal of Organic Chemistry; vol. 62; nb. 16; (1997); p. 5321 - 5326 View in Reaxys

O Cl

Rx-ID: 4870510 View in Reaxys 332/1037 Yield

Conditions & References With chloro-trimethyl-silane, [bis(acetoxy)iodo]benzene, Time= 6h, other reagents, Mechanism Evans, P. Andrew; Brandt, Thomas A.; Journal of Organic Chemistry; vol. 62; nb. 16; (1997); p. 5321 - 5326 View in Reaxys

O O–

I+ O

F F

Rx-ID: 4877229 View in Reaxys 333/1037 Yield

Conditions & References With lithium diisopropyl amide, 1.) THF, -78 deg C, 1 h; 2.) -35 deg C, 15 min, -78 deg C; 3.) -78 deg C, 15 min, r.t., 1 h, Product distribution Ryan, John H.; Stang, Peter J.; Tetrahedron Letters; vol. 38; nb. 28; (1997); p. 5061 - 5064

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View in Reaxys With lithium diisopropyl amide, 1.) THF, -78 deg C, 1 h; 2.) -35 deg C, 15 min, -78 deg C; 3.) -78 deg C, 15 min, r.t., 1 h, Yield given. Multistep reaction Ryan, John H.; Stang, Peter J.; Tetrahedron Letters; vol. 38; nb. 28; (1997); p. 5061 - 5064 View in Reaxys -1 F (v4)

B FF

H +I

I O

Rx-ID: 4881214 View in Reaxys 334/1037 Yield

Conditions & References

60 %, 69 % Chromat., 20 %

With chromium dichloride in N,N-dimethyl-formamide, Time= 5h, T= 25 °C Chen, Da-Wei; Takai, Kazuhiko; Ochiai, Masahito; Tetrahedron Letters; vol. 38; nb. 47; (1997); p. 8211 - 8214 View in Reaxys -1 F (v4)

B FF

I+

Cl Cl

Rx-ID: 4881308 View in Reaxys 335/1037 Yield

Conditions & References

26 %, 26 % Chromat., 31 %

(v4)

B FF

I+

Rx-ID: 4881332 View in Reaxys 336/1037 Yield 42 %, 58 % Chromat., 24 %

Conditions & References With chromium dichloride in N,N-dimethyl-formamide, Time= 5h, T= 25 °C Chen, Da-Wei; Takai, Kazuhiko; Ochiai, Masahito; Tetrahedron Letters; vol. 38; nb. 47; (1997); p. 8211 - 8214

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View in Reaxys Rx-ID: 4912551 View in Reaxys 337/1037 Yield

Conditions & References With n-butyllithium, ethanol in tetrahydrofuran-d8, T= -70 - 30 °C , Product distribution Ochiai, Masahito; Kitagawa, Yutaka; Yamamoto, Shinji; Journal of the American Chemical Society; vol. 119; nb. 48; (1997); p. 11598 - 11604 View in Reaxys

O O

Cl O

O O

Rx-ID: 4919465 View in Reaxys 338/1037 Yield

Conditions & References

50 %

in dichloromethane, acetonitrile, Time= 4h, Ambient temperature, other alkenes, other reaction time, Mechanism De Mico, Antonella; Margarita, Roberto; Parlanti, Luca; Piancatelli, Giovanni; Vescovi, Andrea; Tetrahedron; vol. 53; nb. 49; (1997); p. 16877 - 16882 View in Reaxys -1

F (v4)

B FF

O O

O+

Rx-ID: 5057045 View in Reaxys 339/1037 Yield

Conditions & References With sodium iodide in dimethyl sulfoxide, Time= 5h, T= 90 - 100 °C , Decomposition Tolstaya; Bobyleva; Vanchikov; Kovalysheva; Kulikov; Tsariev; Russian Chemical Bulletin; vol. 46; nb. 4; (1997); p. 789 797 View in Reaxys O

O I

O+

I–

I O

Rx-ID: 5077755 View in Reaxys 340/1037 Yield

Conditions & References Thermolysis, Ring cleavage, dephenylation Tolstaya; Bobyleva; Vanchikov; Kovalysheva; Kulikov; Tsariev; Russian Chemical Bulletin; vol. 46; nb. 4; (1997); p. 789 797 View in Reaxys

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I HO HO

Rx-ID: 5082428 View in Reaxys 341/1037 Yield

Conditions & References With dibenzoyl peroxide, Time= 24h, Heating, deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 - 2632 View in Reaxys

I+ I–

Rx-ID: 5082435 View in Reaxys 342/1037 Yield

Conditions & References

44 %

With chromium(VI) oxide, sulfuric acid, iodine in acetic anhydride, acetic acid, T= 20 - 45 °C , Iodination Lulinski, Piotr; Skulski, Lech; Bulletin of the Chemical Society of Japan; vol. 70; nb. 7; (1997); p. 1665 - 1669 View in Reaxys -1 I+

F F

F (v6)

Sb F F

Rx-ID: 4476653 View in Reaxys 343/1037 Yield

Conditions & References With [D3]acetonitrile, 9,10-diphenylanthracene, Irradiation, var. solvent, reagent, Product distribution, Mechanism Eekert, Gerd; Goez, Martin; Maiwaid, Beate; Mueller, Uwe; Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics; vol. 100; nb. 7; (1996); p. 1191 - 1198 View in Reaxys O

O O–

I+

N–

Li+

F F

N O

Rx-ID: 4554975 View in Reaxys 344/1037 Yield

Conditions & References in hexane, Time= 3h, T= 60 °C , other reaction temperature, Mechanism Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas; Bohnstedt, Adolph C.; Journal of Organic Chemistry; vol. 61; nb. 16; (1996); p. 5440 - 5452 View in Reaxys

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F Si

Rx-ID: 4579685 View in Reaxys 345/1037 Yield

Conditions & References With potassium fluoride, 18-crown-6 ether in dichloromethane, Time= 0.5h, T= 20 °C , Title compound not separated from byproducts Lermontov; Velikohat'ko; Zefirov; Russian Chemical Bulletin; vol. 45; nb. 4; (1996); p. 977 - 978 View in Reaxys OH I

O F

F F

F O

F Cl

Rx-ID: 4603628 View in Reaxys 346/1037 Yield

Conditions & References With iodine in 1,1,2-Trichloro-1,2,2-trifluoroethane, Time= 4h, T= 120 °C , Yield given. Yields of byproduct given Pedersen, Scot D.; Qiu, Weiming; Qiu, Zai-Ming; Kotov, Stefan V.; Burton, Donald J.; Journal of Organic Chemistry; vol. 61; nb. 23; (1996); p. 8024 - 8031 View in Reaxys

O O

O F

Rx-ID: 4619954 View in Reaxys 347/1037 Yield 10 %

Conditions & References With palladium dichloride in water, acetonitrile, Time= 0.5h, Ambient temperature, Yield given. Yields of byproduct given Kang, Suk-Ku; Lee, Hong-Woo; Kim, Jae-Sun; Choi, Sang-Chul; Tetrahedron Letters; vol. 37; nb. 21; (1996); p. 3723 3726 View in Reaxys

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O O

O F F

Rx-ID: 4621442 View in Reaxys 348/1037 Yield

Conditions & References

10 %

With palladium dichloride in water, acetonitrile, Time= 0.333333h, Ambient temperature, Yield given. Yields of byproduct given Kang, Suk-Ku; Lee, Hong-Woo; Kim, Jae-Sun; Choi, Sang-Chul; Tetrahedron Letters; vol. 37; nb. 21; (1996); p. 3723 3726 View in Reaxys

H O H

I H

H O

Rx-ID: 4209211 View in Reaxys 349/1037 Yield

Conditions & References

1 %, 55 %, 1 %, 1 %, 2 %

With dibenzoyl peroxide, Time= 11h, Heating, study of cyclisation with various types and concentrations of initiators, solvents, temperatures, reaction time, Product distribution, Mechanism Mawson; Routledge; Weavers; Tetrahedron; vol. 51; nb. 16; (1995); p. 4665 - 4678 View in Reaxys

F O O O

I Tl

Rx-ID: 4524144 View in Reaxys 350/1037

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Yield

Conditions & References With iodine in acetonitrile, Time= 220h, Ambient temperature Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 65; nb. 3.2; (1995); p. 460; Zhurnal Obshchei Khimii; vol. 65; nb. 3; (1995); p. 518 View in Reaxys

NaOH, H2O

O P

Rx-ID: 6729785 View in Reaxys 351/1037 Yield

Conditions & References With phosphorus, iodine, oxygen, sodium nitrite in toluene, T= 70 - 80 °C , Product distribution, Mechanism Dorfman, Ya. A.; Aleshkova. M. M.; Faizova, F. Kh.; Russian Journal of General Chemistry; vol. 65; nb. 4.1; (1995); p. 508 514; Zhurnal Obshchei Khimii; vol. 65; nb. 4; (1995); p. 570 - 576 View in Reaxys F

–C

O–

FF O–

Tl+

(v0)

Tl3+

Rx-ID: 27229274 View in Reaxys 352/1037 Yield 100 %

Conditions & References in acetonitrile, soln. of iodine addn. to soln. of Tl-compd., mixing, standing (dark, 220h, room temperature), evacuation (under Ar, room temperature, then wate r bath, distillation of I-compd.), product remaining in solid residue Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 65; nb. 3.2; (1995); p. 460; Zhurnal Obshchei Khimii; vol. 65; nb. 3; (1995); p. 518 ; (from Gmelin) View in Reaxys 1

(v4)

C+

Rx-ID: 1709941 View in Reaxys 353/1037 Yield

Conditions & References in acetonitrile, Ambient temperature, Rate constant Yagci, Y.; Schnabel, W.; Wilpert, A.; Bending, J.; Journal of the Chemical Society, Faraday Transactions; vol. 90; nb. 2; (1994); p. 287 - 292 View in Reaxys 1

C+

(v4)

Rx-ID: 1713898 View in Reaxys 354/1037 Yield

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C+

(v4)

Rx-ID: 1742843 View in Reaxys 355/1037 Yield

C+

(v4)

Rx-ID: 1969030 View in Reaxys 356/1037 Yield

C+

(v4)

Rx-ID: 2005601 View in Reaxys 357/1037 Yield

(v4)+

Rx-ID: 2006032 View in Reaxys 358/1037 Yield

(v4)+

Rx-ID: 2007930 View in Reaxys 359/1037 Yield

Conditions & References in acetonitrile, Ambient temperature, Rate constant

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Yagci, Y.; Schnabel, W.; Wilpert, A.; Bending, J.; Journal of the Chemical Society, Faraday Transactions; vol. 90; nb. 2; (1994); p. 287 - 292 View in Reaxys 1

C+

(v4)

Rx-ID: 2008557 View in Reaxys 360/1037 Yield

C+

(v4)

Rx-ID: 2009209 View in Reaxys 361/1037 Yield

(v4)

C+

Rx-ID: 2012223 View in Reaxys 362/1037 Yield

C+

(v4)

Rx-ID: 2013540 View in Reaxys 363/1037 Yield

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C+

(v4)

Rx-ID: 2070588 View in Reaxys 364/1037 Yield

HS O

S S

I S

Rx-ID: 2930643 View in Reaxys 365/1037 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, potassium carbonate, 1.) CH3CN, r.t., 2 min, Yield given. Multistep reaction Kita, Yasuyuki; Okuno, Takayuki; Tohma, Hirofumi; Akai, Shuji; Matsumoto, Keita; Tetrahedron Letters; vol. 35; nb. 17; (1994); p. 2717 - 2720 View in Reaxys 1

(v4)

C+

Rx-ID: 2936790 View in Reaxys 366/1037 Yield

C+

(v4)

Rx-ID: 3361979 View in Reaxys 367/1037 Yield

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C+

(v4)

Rx-ID: 3537417 View in Reaxys 368/1037 Yield

N N

Rx-ID: 3730428 View in Reaxys 369/1037 Yield

Conditions & References With iodine in various solvent(s), Time= 4h, T= 80 °C Wu; Wu, Ziyan; Moore; Moore, Jeffrey S.; Tetrahedron Letters; vol. 35; nb. 31; (1994); p. 5539 - 5542 View in Reaxys With hydrogenchloride, potassium iodide in water, Yield given Foster, Natalie I.; Heindel, Ned D.; Burns, Donald H.; Muhr, William; Synthesis; nb. 7; (1980); p. 572 - 573 View in Reaxys 1

C+

(v4)

Rx-ID: 3861107 View in Reaxys 370/1037 Yield

(v4)+

Rx-ID: 3926232 View in Reaxys 371/1037 Yield

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-1 F (v4)

B FF

Rx-ID: 4273928 View in Reaxys 372/1037 Yield

Conditions & References With tetrabutyl-ammonium chloride, Time= 4h, Heating, other (Z)-(δ-halovinyl)phenyliodonium salts, other reagents, other solvents, var. temp., time, Mechanism Ochiai, Masahito; Oshima, Kunio; Masaki, Yukio; Chemistry Letters; nb. 5; (1994); p. 871 - 874 View in Reaxys

Rx-ID: 1825262 View in Reaxys 373/1037 Yield

Conditions & References With manganese porphyrin in various solvent(s), Time= 4h, T= 20 °C , other manganese reagents, other solvents, Product distribution Neumann, Ronny; Cohen, Moshe; Journal of the Chemical Society, Chemical Communications; nb. 12; (1993); p. 986 - 988 View in Reaxys O

Rx-ID: 2032272 View in Reaxys 374/1037 Yield 77 %

Conditions & References With sodium tetrachloropalladate, sodium carbonate in water, Time= 4.5h, T= 40 °C , Yields of byproduct given Grushin, Vladimir V.; Alper, Hovard; Journal of Organic Chemistry; vol. 58; nb. 18; (1993); p. 4794 - 4795 View in Reaxys -1 I+

F F

F (v6)

P F

Rx-ID: 2519524 View in Reaxys 375/1037 Yield

Conditions & References in acetonitrile, Time= 0.025h, Irradiation, also in the presence of N,N-dimethylaniline, Product distribution, Mechanism Buijsen; Hacker; Tetrahedron Letters; vol. 34; nb. 10; (1993); p. 1557 - 1560 View in Reaxys

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O O

Cl O

F F

Rx-ID: 3755205 View in Reaxys 376/1037 Yield

Conditions & References

60 %

in hexane, dichloromethane Spyroudis, Spyros; Tarantili, Petroula; Journal of Organic Chemistry; vol. 58; nb. 18; (1993); p. 4885 - 4889 View in Reaxys

Si O–

F O

Rx-ID: 3856970 View in Reaxys 377/1037 Yield

Conditions & References

41 %

With n-butyllithium, multistep reaction; other substrates, other alkynes Stang; Blume; Zhdankin; Synthesis; nb. 1; (1993); p. 35 - 36 View in Reaxys

O O I

HNO3+H2SO4

Rx-ID: 18936319 View in Reaxys 378/1037 Yield

Conditions & References Reaction Steps: 2 1: 60 percent / KOH 2: CH2Cl2; hexane With potassium hydroxide in hexane, dichloromethane Spyroudis, Spyros; Tarantili, Petroula; Journal of Organic Chemistry; vol. 58; nb. 18; (1993); p. 4885 - 4889 View in Reaxys Reaction Steps: 2 1: 63 percent / 1.) conc. H2SO4, 2.) aq. HBF4 / acetic anhydride / 2 h / 5 - 10 °C 2: 100 percent Chromat. / NaNO2 / CHCl3; H2O / 0.25 h / 56 °C With tetrafluoroboric acid, sulfuric acid, sodium nitrite in chloroform, water, acetic anhydride Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

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Reaction Steps: 2 Semenov, V. V.; Bruskin, A. B.; Shevelev, S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 12; (1982); p. 2423 - 2427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1982); p. 2741 - 2746 View in Reaxys Reaction Steps: 2 2: 20 °C Semenov, V. V.; Bruskin, A. B.; Shevelev, S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 12; (1982); p. 2423 - 2427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1982); p. 2741 - 2746 View in Reaxys Reaction Steps: 2 1: 87 percent / acetonitrile 2: acetonitrile / 0.45 h / Heating in acetonitrile Lodaya, Jayant S.; Koser, Gerald F.; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 210 - 212 View in Reaxys Reaction Steps: 2 1: 87 percent / acetonitrile 2: acetonitrile / 0.25 h / Ambient temperature in acetonitrile Lodaya, Jayant S.; Koser, Gerald F.; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 210 - 212 View in Reaxys Reaction Steps: 2 1: 89 percent / KOH, MeOH 2: aq. NaHSO3 With methanol, potassium hydroxide, sodium hydrogensulfite Breslow, Ronald; Gellman, Samuel H.; Journal of the American Chemical Society; vol. 105; nb. 22; (1983); p. 6728 - 6729 View in Reaxys Reaction Steps: 2 1: 90 percent / KOH / methanol / -10 °C 2: Cu(acac)2 / 2-methyl-propan-2-ol / Heating; var. solvent; probably irradiation With copper acetylacetonate, potassium hydroxide in methanol, tert-butyl alcohol Hadjiarapoglou, Lazaros; Spyroudis, Spyros; Varvoglis, Anastasios; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 7178 - 7179 View in Reaxys –O

HO N

N+

I CH 2

Rx-ID: 1794948 View in Reaxys 379/1037 Yield

Conditions & References With FeII-EDTA in water, pH 9, Rate constant Gilbert, Bruce C.; Hanson, Peter; Jones, Jason R.; Whitwood, Adrian C.; Timms, Allan W.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 4; (1992); p. 629 - 636 View in Reaxys

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I+

O –O

S O

Rx-ID: 2245777 View in Reaxys 380/1037 Yield

Conditions & References

12 % Chromat., 8 % Chromat.

in dichloromethane, Time= 0.166667h, T= 15 °C , Irradiation, var. solvents; other iodonium salts, Product distribution, Quantum yield, Mechanism Kitamura, Tsugio; Tanaka, Toshimasa; Taniguchi, Hiroshi; Chemistry Letters; nb. 11; (1992); p. 2245 - 2248 View in Reaxys I S

I S

S S S

Rx-ID: 2790792 View in Reaxys 381/1037 Yield

Conditions & References

15 % Spectr., 15 % Spectr., 30 % Spectr.

in N,N-dimethyl-formamide, cathodic reduction (and methylation of the product mixture), Hg cathode, Title compound not separated from byproducts

15 % Spectr., 15 % Spectr., 30 % Spectr.

in N,N-dimethyl-formamide, cathodic reduction (and methylation of the product mixture), Hg cathode, Mechanism

Gade, Thomas; Streek, Michael; Voss, Juergen; Chemische Berichte; vol. 125; nb. 1; (1992); p. 127 - 142 View in Reaxys

N+

I–

Rx-ID: 2926209 View in Reaxys 382/1037 Yield 26 %

Conditions & References in tetrahydrofuran Adcock, James L.; Gakh, Andrei A.; Journal of Organic Chemistry; vol. 57; nb. 23; (1992); p. 6206 - 6210 View in Reaxys

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OH O

Rx-ID: 3087998 View in Reaxys 383/1037 Yield

Conditions & References

149 mg

With [bis(acetoxy)iodo]benzene, iodine in cyclohexane, Time= 2h, Heating, Irradiation Della, Ernest W.; Janowski, Wit K.; Pigou, Paul E.; Australian Journal of Chemistry; vol. 45; nb. 8; (1992); p. 1205 - 1211 View in Reaxys

O–

I+

S +I

O–

P+

F O

Rx-ID: 3448334 View in Reaxys 384/1037 Yield

Conditions & References

70 %

in dichloromethane, Time= 0.5h, Ambient temperature Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys

O–

I+ O

2 F F

O–

2 F

P+

F O

Rx-ID: 3448335 View in Reaxys 385/1037

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Yield

Conditions & References

67 %

in dichloromethane, Time= 0.5h, Ambient temperature Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys

O–

S F +I

I+

O– F

O P+

P+

O F

Rx-ID: 3448336 View in Reaxys 386/1037 Yield

Conditions & References

78 %

in dichloromethane, Time= 0.5h, Ambient temperature Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys

I+ O–

F 2

S F

P F

O I+

O–

P+

S F F

P+

Rx-ID: 3448337 View in Reaxys 387/1037 Yield 94 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature, other bis(phenyliodonium)diyne triflates Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys

94 %

in dichloromethane, Time= 0.5h, Ambient temperature Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864

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View in Reaxys

O–

F 2

I+

O–

P+ O

S F O

P+

Rx-ID: 3448338 View in Reaxys 388/1037 Yield

Conditions & References

76 %

in dichloromethane, Time= 0.5h, Ambient temperature Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys O O I

–O

O Li+

LiI

Rx-ID: 7079940 View in Reaxys 389/1037 Yield

Conditions & References in tetrahydrofuran, Time= 0.0833333h, T= -5 °C , various amounts of nBuLi, other iodine compounds, various organolithium reagents, Product distribution, Mechanism Barton; Jaszberenyi Cs.; Lessmann; Timar; Tetrahedron; vol. 48; nb. 41; (1992); p. 8881 - 8890 View in Reaxys

O–

I+ O

copper-powder

F F

Rx-ID: 20305834 View in Reaxys 390/1037 Yield

Conditions & References Reaction Steps: 2 1: 93 percent / CH2Cl2 / 0.17 h / -78 - 0 °C 2: CH2Cl2 / 0.5 h / Ambient temperature in dichloromethane

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Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys Reaction Steps: 2 1: 90 percent / CH2Cl2 / 0.17 h / -78 - 0 °C 2: CH2Cl2 / 0.5 h / Ambient temperature in dichloromethane Stang, Peter J.; Tykwinski, Rik; Zhdankin, Viktor V.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1861 - 1864 View in Reaxys

N+ N

O– HO

S OO

Rx-ID: 20924883 View in Reaxys 391/1037 Yield

Conditions & References Reaction Steps: 2 1: 46 percent / Na2CO3 / H2O; diethyl ether / 1.) cooling with ice, 10 min, 2.) to r.t. 2: 10 percent Spectr. / dimethylformamide / cathodic reduction (and methylation of the product mixture), Hg cathode With sodium carbonate in diethyl ether, water, N,N-dimethyl-formamide Gade, Thomas; Streek, Michael; Voss, Juergen; Chemische Berichte; vol. 125; nb. 1; (1992); p. 127 - 142 View in Reaxys

Rx-ID: 1729768 View in Reaxys 392/1037 Yield

Conditions & References With iodosylbenzene, δ2-<(n-C4H9)4N>8P2W17O61(Mn3+*Br) in dichloromethane, acetonitrile, Time= 2h, T= 20 °C , other olefins, other transition-metal-substituted polyoxotungstate complexes, Product distribution Mansuy, Daniel; Bartoli, Jean-Francois; Battioni, Pierrette; Lyon, David K.; Finke, Richard G.; Journal of the American Chemical Society; vol. 113; nb. 19; (1991); p. 7222 - 7226 View in Reaxys O

O H

Rx-ID: 1994965 View in Reaxys 393/1037 Yield

Conditions & References

1.3 %

With acetic acid, Time= 72h, Ambient temperature Yang, Yihui; Diederich, Francois; Valentine, Joan Selverstone; Journal of the American Chemical Society; vol. 113; nb. 19; (1991); p. 7195 - 7205 View in Reaxys

O–

I+ O

S F F

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Rx-ID: 2245353 View in Reaxys 394/1037 Yield

Conditions & References in acetone, Irradiation, Quantum yield, Product distribution, Mechanism Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1838 - 1844 View in Reaxys

(v2) I–

Li+

Rx-ID: 2502337 View in Reaxys 395/1037 Yield

Conditions & References in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, T= 0 °C , Equilibrium constant Reich, Hans J.; Green, D. Patric; Phillips, Nancy H.; Journal of the American Chemical Society; vol. 113; nb. 4; (1991); p. 1414 - 1416 View in Reaxys -1 I+

F F

F (v6)

P F

Rx-ID: 2519526 View in Reaxys 396/1037 Yield

Conditions & References in acetone, Irradiation, Product distribution, Mechanism Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1838 - 1844 View in Reaxys

O I+

O S O

O–

OH S O

Rx-ID: 2805161 View in Reaxys 397/1037 Yield

Conditions & References in acetonitrile, Irradiation, Rate constant, Quantum yield, Mechanism

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Naitoh, Kazuhiko; Yamaoka, Tsuguo; Umehara, Akira; Chemistry Letters; nb. 11; (1991); p. 1869 - 1872 View in Reaxys

N N

Rx-ID: 3730427 View in Reaxys 398/1037 Yield

Conditions & References Time= 6h, T= 110 - 120 °C Moore, Jeffrey S.; Weinstein, Edward J.; Wu, Ziyan; Tetrahedron Letters; vol. 32; nb. 22; (1991); p. 2465 - 2466 View in Reaxys O O O

Rx-ID: 3737339 View in Reaxys 399/1037 Yield

Conditions & References With acetic acid, Time= 72h, T= 55 °C Yang, Yihui; Diederich, Francois; Valentine, Joan Selverstone; Journal of the American Chemical Society; vol. 113; nb. 19; (1991); p. 7195 - 7205 View in Reaxys O

H N

I O H

O NH 2

Rx-ID: 3738263 View in Reaxys 400/1037 Yield

Conditions & References

18 %

With [bis(acetoxy)iodo]benzene, Time= 72h, Ambient temperature Yang, Yihui; Diederich, Francois; Valentine, Joan Selverstone; Journal of the American Chemical Society; vol. 113; nb. 19; (1991); p. 7195 - 7205 View in Reaxys

O–

I+ O

F F

H N

Rx-ID: 3738324 View in Reaxys 401/1037

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Yield

Conditions & References Irradiation, Quantum yield, Product distribution, Mechanism Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1838 - 1844 View in Reaxys -1 I+

F F

F (v6)

F F

H N

Rx-ID: 3738453 View in Reaxys 402/1037 Yield

Conditions & References Irradiation, Product distribution, Mechanism Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1838 - 1844 View in Reaxys O O O O O

O O

Rx-ID: 3842114 View in Reaxys 403/1037 Yield

Conditions & References in benzene, Time= 2h, Heating, competition reaction with isopropyl iodide; also with PhN2BF4/i-PrI, p-chlorobenzenediazonium fluoroborate; other alkyl iodides; competition reaction with 1,4-naphthoquinone, Product distribution, Mechanism Coppa, F.; Fontana, F.; Minisci, F.; Barbosa, M. C. Nogueira; Vismara, E.; Tetrahedron; vol. 47; nb. 35; (1991); p. 7343 7352 View in Reaxys

O Cl

Rx-ID: 3855569 View in Reaxys 404/1037

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Yield

Conditions & References

0.9 % Chromat., 1.7 % Chromat., 1.0 % Chromat., 10 % Chromat., 2.6 % Chromat.

With iodosylbenzene, (Et3HN)FeIII(bpb)Cl2 in acetonitrile, Time= 4h, other olefins, other Lewis acids, Product distribution, Mechanism Yang, Yihui; Diederich, Francois; Valentine, Joan Selverstone; Journal of the American Chemical Society; vol. 113; nb. 19; (1991); p. 7195 - 7205 View in Reaxys

N I

Rx-ID: 3863882 View in Reaxys 405/1037 Yield

Conditions & References Time= 6h, T= 110 - 120 °C Moore, Jeffrey S.; Weinstein, Edward J.; Wu, Ziyan; Tetrahedron Letters; vol. 32; nb. 22; (1991); p. 2465 - 2466 View in Reaxys

N I

Rx-ID: 3886087 View in Reaxys 406/1037 Yield

Conditions & References Time= 6h, T= 110 - 120 °C Moore, Jeffrey S.; Weinstein, Edward J.; Wu, Ziyan; Tetrahedron Letters; vol. 32; nb. 22; (1991); p. 2465 - 2466 View in Reaxys Time= 6h, T= 100 - 120 °C , other triazenes; krel Moore, Jeffrey S.; Weinstein, Edward J.; Wu, Ziyan; Tetrahedron Letters; vol. 32; nb. 22; (1991); p. 2465 - 2466 View in Reaxys

I+ Cl –

2-, 3-, and 4-iodobiphenyls

Rx-ID: 8265061 View in Reaxys 407/1037 Yield

Conditions & References in acetonitrile, Irradiation, various anions, Product distribution, Mechanism, Quantum yield Hacker, Nigel P.; Leff, Daniel V.; Dektar, John L.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2280 - 2282 View in Reaxys

I+ Cl –

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H N

2-, 3-, and 4-iodobiphenyls

Rx-ID: 8265239 View in Reaxys 408/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, various anions, Product distribution, Mechanism, Quantum yield Hacker, Nigel P.; Leff, Daniel V.; Dektar, John L.; Journal of Organic Chemistry; vol. 56; nb. 7; (1991); p. 2280 - 2282 View in Reaxys

–N

Na +

Cl N O

Rx-ID: 26672064 View in Reaxys 409/1037 Yield

Conditions & References

14.66 %

in chloroform, acetonitrile, byproducts: NaCl; ICl in CH3CN added over 10-20 min to NaNCO in CH3CN at -10°C under stirring, stirred for 5-10 min, filtered, CHCl3 added, at room temp. Ph3SnCl added dropwise under stirring, refluxed for 2 h; filtered, concd., distilled at 10 mm/Hg, residue crystd. by addition of ether, washed (ether), dried at 30°C/10 mm/Hg; elem. anal. Srivastava; Tangri; Journal of the Indian Chemical Society; vol. 68; nb. 10; (1991); p. 560 - 562 ; (from Gmelin) View in Reaxys

H (v6) (v6) H H HB B HB BBH (v6) (v6) (v6) (v6) (v6) (v6) (v6) (v6) HBB BBH H I B H (v6) H (v6)

(v6)(v6)

(v2)

F–

H (v6) (v6) B BH (v6) HB BH HB (v6) HB BH B– (v6) + FF I B BB (v6) (v6) (v2) H H (v6) F

+ Na (v1)

(v6)

(v6) (v6)

(v6)

(v6) BH(v6) HB BH HB BH (v6) (v6) HB B BHBH F(v6) (v6) (v6) (v6)B H (v6)

(v6)

Rx-ID: 26773586 View in Reaxys 410/1037 Yield

Conditions & References

2 %, 89 %, 2%

in dichloromethane, water, at 40°C, 6 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

(v6) H (v6) H HB B BHI HB B (v6) (v6) (v6) (v6) B B H H B BH HB H (v6) H (v6)

(v6)(v6)

(v2)

H (v6) (v6) B BH (v6) HB BH HB (v6) HB BH B– (v6) + BH FF I B B (v6) (v6) (v2) (v6) H F

+ F– Na (v1)

(v6)

(v6) (v6) (v6)(v6)

(v6) H (v6) H F HB B BH HB B (v6) (v6) (v6) (v6) B B H HB B BH H H (v6) H (v6)

(v6) (v6) (v6)(v6)

(v6)

Rx-ID: 26773587 View in Reaxys 411/1037 Yield <1, 99 %, <0.5

Conditions & References in dichloromethane, water, at 25°C, 0.5 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

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H (v6) (v6) H H HB B HB BBH (v6) (v6) (v6) (v6) (v6) (v6) (v6) (v6) HBB BBH H I B H (v6) H (v6)

(v6)(v6) (v6)

B–

(v6) (v6)

(v6) B HB

BH BH HB BH HB + I B BB (v6) (v6) (v2) H H (v6)

(v6) (v6) (v6)

(v6)

(v6) BH(v6) HB BH HB BH (v6) HB B BHBH F(v6) (v6) (v6) (v6)B H (v6)

(v6)

Rx-ID: 26777097 View in Reaxys 412/1037 Yield

Conditions & References

5 %, 85 %, 7%

With 18-crown-6 ether in chloroform, KF in dry CHCl3 in the presence of 18-crown-6-ether at 25°C, 0.5 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

5 %, 85 %, 7%

With 18-crown-6 ether in dichloromethane, KF in dry CH2Cl2 in the presence of 18-crown-6-ether at 25°C, 0.5 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

H (v6) (v6) H H HB B HB BH (v6) (v6) (v6) (v6) (v6) (v6) (v6) (v6) HBB BBH BH I B H (v6) H (v6)

(v6)(v6)

(v6)

B– FF

(v6) (v6)

(v6) B HB

(v6)

BH HB BH HB + BH I B BB (v6) (v2) H H (v6)

(v6)

(v6) H (v6) H H HB B HB BH (v6) (v6) (v6) (v6) (v6)(v6)B BH B (v6) HB B H F B H (v6) H (v6)

(v6)

Rx-ID: 26777098 View in Reaxys 413/1037 Yield

Conditions & References

2-5, 90-95, 5%

With 18-crown-6 ether in dichloromethane, KF in dry CH2Cl2 in the presence of 18-crown-6 ether at 25°C, 0.1 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

2-5, 90-95, 5%

With 18-crown-6 ether in chloroform, KF in dry CHCl3 in the presence of 18-crown-6 ether at 25°C, 0.1 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

(v6)(v6)

H (v6) F (v6) B BH (v6) HB BH HB (v6) HB BH B– (v6) + FF I B BB (v6) (v6) (v2) H H (v6) (v6)

FNa

H (v6) (v6) H H HB B HB BBH (v6) (v6) (v6) (v6) (v6) (v6) (v6) (v6) HBB BBH H I B H (v6) H (v6)

(v6) (v6) (v6)

(v6)

(v6) BH(v6) HB BH HB BH (v6) HB BH B BH F(v6) (v6) (v6) (v6)B H (v6)

(v6)

Rx-ID: 26777258 View in Reaxys 414/1037 Yield

Conditions & References

7 %, 75 %, 5%

in chloroform, water, mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaF, water and chloroform was vigorously stirred under reflux at 56°C, 1 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

(v6)(v6)

(v6)

B– FF

(v6) (v6)

(v6) B HB

BH BH HB BH HB + BH I B B (v6) (v2) (v6) H

(v6) (v6)

FNa

(v6)

(v6) H (v6) H HB B BHI HB B (v6) (v6) (v6) (v6) (v6) (v6)(v6) B BH B (v6) HB B H H H (v6) H (v6)

(v6) H (v6) H F HB B BH HB B (v6) (v6) (v6) (v6) (v6) (v6)(v6) B BH B (v6) HB B H H H (v6) H (v6)

(v6)

Rx-ID: 26777259 View in Reaxys 415/1037

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Yield

Conditions & References

0 %, 99.5 %, <0.5

in dichloromethane, water, 25°C, 0.6 h Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

(v6) H (v6) H F HB B BH HB B (v6) (v6) (v6) (v6) (v6) (v6) (v6)(v6) B B H H B BH HB H (v6) H (v6)

(v6)(v6)

H (v6) F (v6) B BH (v6) HB BH HB (v6) HB BH B– (v6) + BH FF I B B (v6) (v6) (v2) H (v6) (v6)

FNa

Cl I Cl

(v6)

Rx-ID: 26777260 View in Reaxys 416/1037 Yield

Conditions & References

99.5 %, 70 %

With sodium fluoride in dichloromethane, water, mixt. of iodonium salt, NaF, H2O and CH2Cl2 stirred at 25°C for 35 min; org. phase sepd. off, filtered through a short alumina plug and evapd., the residue is a mixt. of C6H5I and 2-fluoro-p-carborane; solid dissolved in dry CCl4; soln. satd. with Cl2 at 5°C, and then evapd., to give the mixt. of C6H3Cl2I and the fluorocarborane; the latter extd. with pentane, filtered through an alumina plug, evapd. to dryness, vac. sublimation; elem. anal. Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

(v6) H (v6) H HB B BH HB BH (v6) (v6) (v6) (v6) (v6) (v6)(v6)B B H H B H ClB B H (v6) H (v6)

(v6)(v6)

H (v6) F (v6) B BH (v6) HB BH HB (v6) HB BH B– (v6) + FF I B BB (v6) (v6) (v2) H H (v6) (v6)

ClNa

(v6)

Rx-ID: 26778103 View in Reaxys 417/1037 Yield 100 %

Conditions & References in chloroform, water, mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaF, water and chloroform was vigorously stirred under reflux at 56°C, 1 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 4860 - 4863 ; (from Gmelin) View in Reaxys

Pb Pb

I2Pb

Rx-ID: 26857758 View in Reaxys 418/1037 Yield 72 %, 90 %

Conditions & References With I2 in chloroform-d1, (N2), stirred, treated with 6 equiv I2 at 25°C; filtered; NMR, IR, mass. spectra Kobayashi, Michio; Latour, Stephan; Wuest, James D.; Organometallics; vol. 10; (1991); p. 2908 - 2913 ; (from Gmelin) View in Reaxys

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I2Pb

Rx-ID: 26857792 View in Reaxys 419/1037 Yield

Conditions & References

>99, 94 %

With I2 in chloroform-d1, (N2), stirred, treated with 3 equiv I2 at 0°C; filtered; NMR, iodobenzene : 1-iodopropane = 3:1 Kobayashi, Michio; Latour, Stephan; Wuest, James D.; Organometallics; vol. 10; (1991); p. 2908 - 2913 ; (from Gmelin) View in Reaxys

N N –N

Na +

Sn Cl

Rx-ID: 26867390 View in Reaxys 420/1037 Yield

Conditions & References

19.06 %

in chloroform, acetonitrile, byproducts: NaCl; ICl in CH3CN added over 10-20 min to NaN3 in CH3CN at -10°C under stirring, stirred for 5-10 min, filtered, CHCl3 added, at room temp. Ph3SnCl added dropwise under stirring, refluxed for 2 h; filtered, concd., distilled at 10 mm/Hg, residue crystd. by addition of ether, washed (ether), dried at 30°C/10 mm/Hg; elem. anal. Srivastava; Tangri; Journal of the Indian Chemical Society; vol. 68; nb. 10; (1991); p. 560 - 562 ; (from Gmelin) View in Reaxys

S– Na +

Sn Cl

Rx-ID: 26871407 View in Reaxys 421/1037 Yield 14 %

Conditions & References in chloroform, acetonitrile, byproducts: NaCl; ICl in CH3CN added over 10-20 min to NaNCS in CH3CN at -10°C under stirring, stirred for 5-10 min, filtered, CHCl3 added, at room temp. Ph3SnCl added dropwise under stirring, refluxed for 2 h; filtered, concd., distilled at 10 mm/Hg, residue crystd. by addition of ether, washed (ether), dried at 30°C/10 mm/Hg; elem. anal. Srivastava; Tangri; Journal of the Indian Chemical Society; vol. 68; nb. 10; (1991); p. 560 - 562 ; (from Gmelin) View in Reaxys

I2Pb

Rx-ID: 26935263 View in Reaxys 422/1037 Yield 85 %, 93 %

Conditions & References With I2 in chloroform-d1, (N2), stirred, treated with 3 equiv I2 at 25°C; filtered; NMR, IR, mass. spectra Kobayashi, Michio; Latour, Stephan; Wuest, James D.; Organometallics; vol. 10; (1991); p. 2908 - 2913 ; (from Gmelin) View in Reaxys

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I N

Rx-ID: 1975012 View in Reaxys 423/1037 Yield

Conditions & References With cation exchange resin BioRad AG 50W-X12 (H+), sodium iodide in acetonitrile, T= 75 °C , further solvent: THF, DMSO, Product distribution Barrio, Jorge R.; Satyamurthy, Nagichettiar; Ku, Hao; Phelps, Michael E.; Journal of the Chemical Society, Chemical Communications; nb. 8; (1983); p. 443 - 444 View in Reaxys With chloro-trimethyl-silane, sodium iodide in acetonitrile, Time= 0.0833333h, T= 60 °C Ku, Hao; Barrio, Jorge R.; Journal of Organic Chemistry; vol. 46; (1981); p. 5239 - 5241 View in Reaxys With diiodomethane, isopentyl nitrite, 1.) room temperature, 30 min, 2.) 80 deg C, 4 h Smith,William B.; Ho, Oliver Chenpu; Journal of Organic Chemistry; vol. 55; nb. 8; (1990); p. 2543 - 2545 View in Reaxys

-1 F

(v4)

B FF

F F

N+ N

Rx-ID: 2018572 View in Reaxys 424/1037 Yield

Conditions & References

11 %

With potassium iodide in water, acetone, T= 0 - 15 °C Ganushchak, N. I.; Bilaya, E. E.; Obushak, N. D.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 2.2; (1990); p. 403 405,347 - 349 View in Reaxys

(v1)

–Cl

(v2)

Hg +

Rx-ID: 2214852 View in Reaxys 425/1037 Yield

Conditions & References With iodine, potassium iodide, Time= 0.5h, T= 80 °C Niemyjska, Maria; Skulski, Lech; Zdrojewska, Hanna; Bulletin of the Polish Academy of Sciences, Chemistry; vol. 38; nb. 1-12; (1990); p. 41 - 46 View in Reaxys

I+ Cl –

Rx-ID: 2241024 View in Reaxys 426/1037

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Yield

Conditions & References in water, acetone, Irradiation, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys

O–

I+ O

F O

Rx-ID: 2245348 View in Reaxys 427/1037 Yield

Conditions & References in acetonitrile, Irradiation, 0.02m chlorobenzene, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys

O–

I+ O

F O

Rx-ID: 2245349 View in Reaxys 428/1037 Yield

Conditions & References With xanth-9-one in acetonitrile, Irradiation, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys

O–

I+ O

F O

Rx-ID: 2245350 View in Reaxys 429/1037 Yield

Conditions & References With anthracene in acetonitrile, Irradiation, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys With benzophenone in acetonitrile, Irradiation, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys

O–

I+ O

F F

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Rx-ID: 2245351 View in Reaxys 430/1037 Yield

Conditions & References in methanol, Irradiation, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys

O–

I+ O

F O

H N

Rx-ID: 2245352 View in Reaxys 431/1037 Yield

Conditions & References in acetonitrile, Irradiation, Product distribution Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 639 - 647 View in Reaxys

H N

Rx-ID: 3402883 View in Reaxys 432/1037 Yield

Conditions & References With diiodomethane, isopentyl nitrite, Time= 2.5h, T= 80 °C Smith,William B.; Ho, Oliver Chenpu; Journal of Organic Chemistry; vol. 55; nb. 8; (1990); p. 2543 - 2545 View in Reaxys

O S

O O

O S

S I

Rx-ID: 3740539 View in Reaxys 433/1037 Yield

Conditions & References

28.5 % in acetonitrile, Time= 0.75h, T= 80 °C , also with <hydroxy(tosyloxy)iodo>benzene, <hydroxy(mesyloxy)iodo>benzene, ProdSpectr., 66.6 uct distribution % Spectr. Hatzigrigoriou, Evangelia; Varvoglis, Anastasios; Bakola-Christianopoulou, Maria; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 315 - 318 View in Reaxys

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28.5 % in acetonitrile, Time= 0.75h, T= 80 °C , other carbonyl compounds, other solvents, other time, other temp., Product distribution Spectr., 66.6 Hatzigrigoriou, Evangelia; Varvoglis, Anastasios; Bakola-Christianopoulou, Maria; Journal of Organic Chemistry; vol. 55; % Spectr. nb. 1; (1990); p. 315 - 318 View in Reaxys

I O

O O

H N

Rx-ID: 3854745 View in Reaxys 434/1037 Yield

Conditions & References With iron(III) trifluoromethanesulfonate in acetonitrile, Time= 2h, Ambient temperature, other metal complexes, Product distribution, Mechanism Yang, Yihui; Diederich, Francois; Valentine, Joan Selverstone; Journal of the American Chemical Society; vol. 112; nb. 21; (1990); p. 7826 - 7828 View in Reaxys

I+

O P

–O

S O

O O

S O

Rx-ID: 3873540 View in Reaxys 435/1037 Yield

Conditions & References

90 %, 96 %

Time= 0.0166667h, Ambient temperature, other alkynyl (phenyl)iodonium tosylates (iodobenzene GC yields), Mechanism Lodaya, Jayant S.; Koser, Gerald F.; Journal of Organic Chemistry; vol. 55; nb. 5; (1990); p. 1513 - 1516 View in Reaxys H N

N N

Rx-ID: 3878592 View in Reaxys 436/1037 Yield

Conditions & References With chloro-trimethyl-silane, sodium iodide in acetonitrile, Time= 0.25h, T= 60 °C Smith,William B.; Ho, Oliver Chenpu; Journal of Organic Chemistry; vol. 55; nb. 8; (1990); p. 2543 - 2545 View in Reaxys

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Cl B Li

Cl 2Hg

Rx-ID: 26672066 View in Reaxys 437/1037 Yield

Conditions & References in tetrahydrofuran, diethyl ether, inert atmosphere; refluxing of boron derivative and MeLi (1 h), addn. of HgCl2 in MeOH/H2O, addn. of ICl, refluxing; neutralizing (aq. NaHCO3), extn. (Et2O), drying (MgSO4), evapn., chromy. (Al2O3) Eisch, John J.; Galle, James E.; Shafii, Babak; Rheingold, Arnold L.; Organometallics; vol. 9; (1990); p. 2342 - 2349 ; (from Gmelin) View in Reaxys

Se O

Sn Sn

Se I O

Rx-ID: 26740924 View in Reaxys 438/1037 Yield

Conditions & References With I2 in tetrachloromethane, room temp.; (1)H-NMR Cox, Philip J.; Doidge-Harrison, Solange M. S. V.; Nowell, Ian W.; Howie, R. Alan; Randall, Andrew P.; Wardell, James L.; Inorganica Chimica Acta; vol. 176; (1990); p. 155 - 162 ; (from Gmelin) View in Reaxys

Rx-ID: 31260716 View in Reaxys 439/1037 Yield

Conditions & References Reaction Steps: 2 1: toluene 2: tetrahydrofuran; diethyl ether in tetrahydrofuran, diethyl ether, toluene Eisch, John J.; Galle, James E.; Shafii, Babak; Rheingold, Arnold L.; Organometallics; vol. 9; (1990); p. 2342 - 2349 View in Reaxys O

S O

I O

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S O O

O O

Rx-ID: 2155444 View in Reaxys 440/1037 Yield

Conditions & References

48 %, 20 %

With copper acetylacetonate, Time= 0.166667h, T= 100 °C , Mechanism Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

48 %, 20 %

With copper acetylacetonate, Time= 0.166667h, T= 100 °C Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys O

O I

O O

I O

O S

S O O

Rx-ID: 2155446 View in Reaxys 441/1037 Yield

Conditions & References

26 %

With copper acetylacetonate, Time= 0.0833333h, T= 110 °C , Mechanism Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

26 %

With copper acetylacetonate, Time= 0.0833333h, T= 110 °C Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

O S

I Cl

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S S

O O

Rx-ID: 2155447 View in Reaxys 442/1037 Yield

Conditions & References

42 %

With copper acetylacetonate, Time= 0.25h, T= 120 °C Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

42 %

With copper acetylacetonate, Time= 0.25h, T= 120 °C , Mechanism Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

N O

I–

I I

Rx-ID: 2635708 View in Reaxys 443/1037 Yield

Conditions & References

78 %

heated in an oil-bath until it melted with decomposition Kotali, Elvira; Varvoglis, Anastassios; Bozopoulos, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1989); p. 827 - 832 View in Reaxys

I+

I–

I I

Rx-ID: 2636780 View in Reaxys 444/1037 Yield 95 %

Conditions & References heated in an oil-bath until it melted with decomposition Kotali, Elvira; Varvoglis, Anastassios; Bozopoulos, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1989); p. 827 - 832

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View in Reaxys

O O

O S

O I

O S O

Rx-ID: 2671838 View in Reaxys 445/1037 Yield

Conditions & References With tetraphenylethane-1,2-diol in dichloromethane, Time= 12h, Ambient temperature, other reagents at various reaction times Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys With styrene in acetonitrile, Time= 1.25h, Irradiation, other reagents at variuos reaction times Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys With tetraphenylethane-1,2-diol in dichloromethane, Time= 12h, Ambient temperature, some thermal and photochemical oxydation reactions with various substrates Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys -1

F (v4)

B FF

F F

I+

F O

F F

Rx-ID: 3421279 View in Reaxys 446/1037 Yield

Conditions & References

40 % Chromat.

With cesium fluoride in acetonitrile, Time= 168h, T= 80 °C , Yields of byproduct given German, L. S.; Delyagina, N. I.; Vanchikov, A. N.; Tolstaya, T. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 1.2; (1989); p. 174 - 176; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 38; nb. 1; (1989); p. 188 - 190 View in Reaxys

O HO I+

OH O

O–

Rx-ID: 3495805 View in Reaxys 447/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, Quantum yield Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460

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View in Reaxys S

O O S

S O

I O

Rx-ID: 3867871 View in Reaxys 448/1037 Yield

Conditions & References

83 %

I O S O

S O

S S

O O

Rx-ID: 3867873 View in Reaxys 449/1037 Yield 5%

Conditions & References With copper acetylacetonate Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

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O O

O S

I O

S S

O O

Rx-ID: 3867874 View in Reaxys 450/1037 Yield

Conditions & References

35 %

O S

I Cl

S S

O O

Rx-ID: 3867875 View in Reaxys 451/1037 Yield 44 %

Conditions & References With copper acetylacetonate, Time= 0.166667h, T= 110 °C

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Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys 44 %

With copper acetylacetonate, Time= 0.166667h, T= 110 °C , Mechanism Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

S O S O I O S O

S S

I O

Rx-ID: 3867877 View in Reaxys 452/1037 Yield

Conditions & References

39 %

O S O I O S O

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O O

S S

Rx-ID: 3934628 View in Reaxys 453/1037 Yield 27 %

Conditions & References With copper acetylacetonate, Time= 0.333333h, T= 120 °C Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

27 %

With copper acetylacetonate, Time= 0.333333h, T= 120 °C , Mechanism Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1989); p. 379 - 382 View in Reaxys

I+ Cl –

–O

Na +

C6H5C6H4I, C6H4I2, C6H5C6H4OCH3, C6H4IOCH3

Rx-ID: 8270488 View in Reaxys 454/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, Product distribution Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460 View in Reaxys

I+ Cl –

H N HO

C6H5C6H4I

Rx-ID: 8270489 View in Reaxys 455/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, other solvents, dependence of quantum yield from the light intensity, Product distribution, Quantum yield, Mechanism Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460 View in Reaxys

163/330

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O– I+

S OO

H2SO4 Rx-ID: 8276494 View in Reaxys 456/1037

Yield

Conditions & References in water, acetonitrile, Irradiation, Quantum yield Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460 View in Reaxys -1

F (v4)

B FF

HBF4

I+

Rx-ID: 8276527 View in Reaxys 457/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, Quantum yield Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460 View in Reaxys

I+ Br–

HBr

Rx-ID: 8276535 View in Reaxys 458/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, Quantum yield Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460 View in Reaxys

I+ I–

Rx-ID: 8277118 View in Reaxys 459/1037 Yield

Conditions & References in water, acetonitrile, Irradiation, Quantum yield Timpe, H.-J.; Schikowsky, V.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 447 - 460 View in Reaxys

H H

(v5)H

(v5)

F F

B– FF

Re (v8) (v2)

Br–

N+

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-1 F (v4)

H H

I O

(v5)

B FF

(v5)

(v5)H

(v5)

(v8)

N+

(v4)

Rx-ID: 26593255 View in Reaxys 460/1037 Yield

Conditions & References in dichloromethane-d2, (N2); react. of Re complex and Ph3PNPPh3(1+) in CD2Cl2 at room temp. within 5 min; not isolated, detected by (13)C- and (31)P-NMR Winter, Charles H.; Veal, William R.; Garner, Charles M.; Arif, Atta M.; Gladysz, J. A.; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4766 - 4776 ; (from Gmelin) View in Reaxys O– 2 O (v3)

Cl OO

(v4)2+ Fe

(v3) (v3)

(v3)

O P

O– 4 (v3)

OH 2

Cl OO

(v3) OH 2 (v3)

Fe 4+

(v3) (v3)

(v6)

P (v3)

(v3) (v6)

(v3)

P (v3)

O O

(v3)

Rx-ID: 26597681 View in Reaxys 461/1037 Yield 87.2 %

Conditions & References With C6H5I(CH3COO)2 in acetonitrile, to soln. of Fe complex was added oxygenating agent (5-fold excess) and stirred for 30 min (H2O2 required several h for completion); soln. added slowly to great excess of ether, purple ppt. was formed; ppt. filtered, washed with ether and dried over BaSO4 or P2O5 in vac. for several days; elem. anal. Sawyer, Donald T.; McDowell, M. Steven; Spencer, Lee; Tsang, Paul K. S.; Inorganic Chemistry; vol. 28; (1989); p. 1166 1170 ; (from Gmelin) View in Reaxys

87.2 %

With C6H5IO in acetonitrile, to soln. of Fe complex was added oxygenating agent (5-fold excess) and stirred for 30 min (H2O2 required several h for completion); soln. added slowly to great excess of ether, purple ppt. was formed; ppt. filtered, washed with ether and dried over BaSO4 or P2O5 in vac. for several days; elem. anal. Sawyer, Donald T.; McDowell, M. Steven; Spencer, Lee; Tsang, Paul K. S.; Inorganic Chemistry; vol. 28; (1989); p. 1166 1170 ; (from Gmelin) View in Reaxys

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Rx-ID: 1504229 View in Reaxys 462/1037 Yield

O S O I O S O

O O S

I O

Rx-ID: 1546140 View in Reaxys 463/1037 Yield 11 %, 68 %

Conditions & References in acetonitrile, Time= 1.25h, Irradiation Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys

I+

N N

–O

N O

Rx-ID: 1584226 View in Reaxys 464/1037 Yield 20 %

Conditions & References With sodium azide, -70 deg C then rt.; through alkylidenecarbene-iodonium ylides intermediate, Mechanism Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

20 %

With sodium azide, -70 deg C then rt. Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

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I+

O SiH

–O

S O

N Si

N N

Rx-ID: 1608654 View in Reaxys 465/1037 Yield

Conditions & References With sodium azide, 18-crown-6 ether, -70 deg C then rt.; through alkylidenecarbene-iodonium ylides intermediate, Mechanism, Product distribution Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

I+

O SiH

–O

S O

N Si

I N N N

Rx-ID: 1608879 View in Reaxys 466/1037 Yield

Conditions & References With sodium azide, 18-crown-6 ether in dichloromethane, -70 deg C then rt.; through alkylidenecarbene-iodonium ylides intermediate, Mechanism, Product distribution Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys With sodium azide, 18-crown-6 ether in dichloromethane, -70 deg C then rt., Yield given. Yields of byproduct given Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

N O

Rx-ID: 1626142 View in Reaxys 467/1037 Yield 1 % Chromat.

Conditions & References With 3,3-dimethyl-butan-2-one, potassium tert-butylate in ammonia, Time= 0.583333h, T= -33 °C , Irradiation Galli, Carlo; Tetrahedron; vol. 44; nb. 16; (1988); p. 5205 - 5208 View in Reaxys

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I+

O O

–O

S O

N N

Rx-ID: 1690916 View in Reaxys 468/1037 Yield 63 %

Conditions & References With triethylsilane, sodium azide, 18-crown-6 ether, -70 deg C then rt., Yields of byproduct given Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

O– S

I+

O O O O

O O

O S

O O

Rx-ID: 1691465 View in Reaxys 469/1037 Yield 15 %

Conditions & References in dichloromethane, T= 0 °C Semerikov, V. N.; Sorokin, V. D.; Zhdankin, V. V.; Koz'min, A. S.; Zefirov, N. S.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 4; (1988); p. 802 - 803; Zhurnal Organicheskoi Khimii; vol. 24; nb. 4; (1988); p. 888 - 889 View in Reaxys

I O O

O O

N O

Rx-ID: 1697908 View in Reaxys 470/1037 Yield

Conditions & References With potassium tert-butylate in ammonia, T= -33 °C , effect of irradiation, inhibitor and reaction time, Product distribution, Mechanism Galli, Carlo; Tetrahedron; vol. 44; nb. 16; (1988); p. 5205 - 5208

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View in Reaxys F F

Rx-ID: 1711213 View in Reaxys 471/1037 Yield

Conditions & References With 1-methyl-pyrrolidin-2-one, copper(l) iodide, sodium 2,2,2-trifluoroacetate, Time= 4h, T= 160 °C Carr, Gillian E.; Chambers, Richard D.; Holmes, Thomas F.; Parker, David G.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 921 - 926 View in Reaxys

S O I

S O

Rx-ID: 1761279 View in Reaxys 472/1037 Yield 30 %

Conditions & References in acetonitrile, Time= 6.5h, Irradiation Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys O I

Rx-ID: 1806551 View in Reaxys 473/1037 Yield

Conditions & References

0.4 % Chro- With 3,3-dimethyl-butan-2-one, potassium tert-butylate in ammonia, Time= 0.583333h, T= -33 °C , Irradiation mat., 2 % Galli, Carlo; Tetrahedron; vol. 44; nb. 16; (1988); p. 5205 - 5208 Chromat. View in Reaxys

O O

O I

S O

Rx-ID: 1976878 View in Reaxys 474/1037 Yield 69 %

Conditions & References in acetonitrile, Time= 1.2h, Irradiation

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Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys O

O O

S S

I O

Rx-ID: 1994948 View in Reaxys 475/1037 Yield

Conditions & References With potassium hydroxide, multistep reaction, Product distribution Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys

Rx-ID: 2011244 View in Reaxys 476/1037 Yield

Conditions & References With potassium carbonate, iron pentacarbonyl in methanol, Time= 48h, T= 60 °C , p= 760Torr Brunet, Jean-Jacques; Taillefer, Marc; Journal of Organometallic Chemistry; vol. 348; (1988); p. C5 - C8 View in Reaxys -1 I+

F F

F (v6)

P F

Rx-ID: 2012515 View in Reaxys 477/1037 Yield

Conditions & References in acetonitrile, Irradiation, Quantum yield DeVoe, R. J.; Sahyun, R. V.; Schmidt, Einhard; Serpone, N.; Sharma, D. K.; Canadian Journal of Chemistry; vol. 66; (1988); p. 319 - 324 View in Reaxys

O O

I N

O O

N O

Rx-ID: 2065182 View in Reaxys 478/1037

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Yield

Conditions & References

17 % Chromat., 19 % Chromat.

With 3,3-dimethyl-butan-2-one, di-tert-butyl nitroxide, potassium tert-butylate in ammonia, Time= 0.025h, T= -33 °C Galli, Carlo; Tetrahedron; vol. 44; nb. 16; (1988); p. 5205 - 5208 View in Reaxys

O S O

Rx-ID: 2076523 View in Reaxys 479/1037 Yield

Conditions & References

53 %

in dichloromethane, Time= 12h Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys -1 F (v4)

B FF

(v2) Cu –

Li+

Rx-ID: 2212666 View in Reaxys 480/1037 Yield 84 % Chromat.

Conditions & References in diethyl ether, Time= 3h, T= -78 °C Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys

O Na + O–

I+

O –O

S O

171/330

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I O

Rx-ID: 2239062 View in Reaxys 481/1037 Yield

Conditions & References

40 %

in dichloromethane, on benzoate loaded Amberlyst column Stang,P.J.; Boeshar,M.; Wingert,H.; Journal of the American Chemical Society; vol. 110; (1988); p. 3272 View in Reaxys

I+

Na + O

–O

–

I O

Rx-ID: 2239063 View in Reaxys 482/1037 Yield

Conditions & References

16 %

in dichloromethane, on benzoate loaded Amberlyst column Stang,P.J.; Boeshar,M.; Wingert,H.; Journal of the American Chemical Society; vol. 110; (1988); p. 3272 View in Reaxys -1 F (v4)

F (v2)

Cu –

B FF

Li+

Rx-ID: 2253242 View in Reaxys 483/1037 Yield

Conditions & References

73 % Chromat.

in tetrahydrofuran, Time= 4h, T= -78 °C Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys

O– I+ HO

S OO

Rx-ID: 2327622 View in Reaxys 484/1037 Yield

Conditions & References With tert-butylchlorodiphenylsilane in n-heptane, water, Time= 2h, Irradiation, Quantum yield Kronfeld, K.-P.; Timpe, H.-J.; Journal fuer Praktische Chemie (Leipzig); vol. 330; nb. 4; (1988); p. 571 - 584 View in Reaxys

172/330

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-1 F (v4)

B FF

I+ F

F F

F F F

F F

F F F

F F

Rx-ID: 2469787 View in Reaxys 485/1037 Yield

Conditions & References

89 %

Time= 4h, T= 150 - 160 °C , sealed tube Mironova, A. A.; Soloshonok, I. V.; Maletina, I. I.; Orda, V. V.; Yagupol'skii, L. M.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 3; (1988); p. 530 - 535; Zhurnal Organicheskoi Khimii; vol. 24; nb. 3; (1988); p. 593 - 598 View in Reaxys -1 I+

F F

F (v6)

P F

Rx-ID: 2519522 View in Reaxys 486/1037 Yield

Conditions & References in methanol, Time= 0.05h, T= 0 °C , Irradiation, also triarylsulfonium salt; other solvents and irradiation time Ma, Xiao-Hua; Yamamoto, Yukio; Hayashi, Koichiro; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5443 - 5445 View in Reaxys

O O

S O S O

S O

Rx-ID: 2592173 View in Reaxys 487/1037 Yield

Conditions & References With copper acetylacetonate in tert-butyl alcohol, Time= 5h, Heating

O O S

O S

O S S

Rx-ID: 2609322 View in Reaxys 488/1037 Yield 55 %, 22 %

Conditions & References With copper acetylacetonate in tert-butyl alcohol, Time= 5h, Heating

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O S

Rx-ID: 2613296 View in Reaxys 489/1037 Yield

Conditions & References With copper acetylacetonate in tert-butyl alcohol, Time= 5h, Heating

47 %

O S

Rx-ID: 2613297 View in Reaxys 490/1037 Yield

Conditions & References With copper acetylacetonate in tert-butyl alcohol, Time= 5h, Heating

55 %

(v4)

B FF

Rx-ID: 2634290 View in Reaxys 491/1037 Yield 0.2 % Chromat., 25 % Chromat., 17 % Chromat.

Conditions & References With n-butyllithium in tetrahydrofuran, hexane, Time= 3h, T= -78 °C Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al.; Tetrahedron; vol. 44; nb. 13; (1988); p. 4095 - 4112 View in Reaxys

174/330

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O –O

S O

N N N

Rx-ID: 2638094 View in Reaxys 492/1037 Yield

Conditions & References

58 %

With sodium azide in dichloromethane, -70 deg C then rt. Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

58 %

With sodium azide in dichloromethane, -70 deg C then rt.; through alkylidenecarbene-iodonium ylides intermediate, Mechanism Kitamura, Tsugio; Stang, Peter J.; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1887 - 1890 View in Reaxys

S O I O

S O

Rx-ID: 2671837 View in Reaxys 493/1037 Yield 80 %

Conditions & References With copper acetylacetonate in tert-butyl alcohol, Time= 5h, Heating Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys

80 %

With copper acetylacetonate in tert-butyl alcohol, Heating, var. solvent; probably irradiation, Mechanism Hadjiarapoglou, Lazaros; Spyroudis, Spyros; Varvoglis, Anastasios; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 7178 - 7179 View in Reaxys

Rx-ID: 2856672 View in Reaxys 494/1037 Yield

Conditions & References Time= 24h, Irradiation, addition of Et3N, other alkyl iodides, var. solvents, other arenes, Product distribution, Mechanism Kurz, Michael E.; Noreuil, Tim; Seebauer, Joe; Cook, Stephanie; Geier, Douglas; et al.; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 172 - 177 View in Reaxys

175/330

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Rx-ID: 2936858 View in Reaxys 495/1037 Yield

Rx-ID: 2936859 View in Reaxys 496/1037 Yield

Conditions & References

36 %

With boron trifluoride diethyl etherate in dichloromethane, T= -25 °C Lee, Kilsung; Kim, Dae Young; Oh, Dong Young; Tetrahedron Letters; vol. 29; nb. 6; (1988); p. 667 - 668 View in Reaxys

O O

O– S

O O

I+

O O

Rx-ID: 2990247 View in Reaxys 497/1037 Yield

Conditions & References in dichloromethane, T= 20 °C Semerikov, V. N.; Sorokin, V. D.; Zhdankin, V. V.; Koz'min, A. S.; Zefirov, N. S.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 4; (1988); p. 802 - 803; Zhurnal Organicheskoi Khimii; vol. 24; nb. 4; (1988); p. 888 - 889 View in Reaxys

F O

F F

F Br

Cl O–

OH Br

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HN Br

F O

Rx-ID: 3025588 View in Reaxys 498/1037 Yield

Conditions & References With copper, triethylamine in dichloromethane, Time= 18h, Ambient temperature, Yield given Hickey, Deirdre M. B.; Leeson, Paul D.; Novelli, Riccardo; Shah, Virendra P.; Burpitt, Brian E.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 3103 - 3112 View in Reaxys -1

F (v4)

B FF

H 2N

I+ F

F F

-1

F F

H N

(v4)

B FF

NH 2

H+

Rx-ID: 3373184 View in Reaxys 499/1037 Yield

Conditions & References

100 %, 87 %

in dichloromethane, 1) 0 deg C, 2 h, 2) 20 deg C, 1 h Mironova, A. A.; Soloshonok, I. V.; Maletina, I. I.; Orda, V. V.; Yagupol'skii, L. M.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 3; (1988); p. 530 - 535; Zhurnal Organicheskoi Khimii; vol. 24; nb. 3; (1988); p. 593 - 598 View in Reaxys

I O S O

S O

Rx-ID: 3405426 View in Reaxys 500/1037 Yield 32 %

Conditions & References in dichloromethane, Time= 12h Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys

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O O S

O S

I O S O

Rx-ID: 3405429 View in Reaxys 501/1037 Yield

Conditions & References

47 %

O S O I O S O

I O S O

Rx-ID: 3405446 View in Reaxys 502/1037 Yield 61 %

178/330

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Rx-ID: 3537487 View in Reaxys 503/1037 Yield

Conditions & References With iodosylbenzene, boron trifluoride diethyl etherate in dichloromethane, Time= 3h, Ambient temperature, Yield given. Yields of byproduct given Lee, Kilsung; Kim, Dae Young; Oh, Dong Young; Tetrahedron Letters; vol. 29; nb. 6; (1988); p. 667 - 668 View in Reaxys With iodosylbenzene, boron trifluoride diethyl etherate in dichloromethane, Time= 3h, Ambient temperature, Yield given. Yields of byproduct given Lee, Kilsung; Kim, Dae Young; Oh, Dong Young; Tetrahedron Letters; vol. 29; nb. 6; (1988); p. 667 - 668 View in Reaxys HO

S O

I S

Rx-ID: 3740693 View in Reaxys 504/1037 Yield

Conditions & References in acetonitrile, Time= 0.45h, Heating, Yield given. Yields of byproduct given. Title compound not separated from byproducts Lodaya, Jayant S.; Koser, Gerald F.; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 210 - 212 View in Reaxys O

O S

I S

Rx-ID: 3744258 View in Reaxys 505/1037 Yield

Conditions & References

60 %

in acetonitrile, Time= 0.25h, Ambient temperature Lodaya, Jayant S.; Koser, Gerald F.; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 210 - 212 View in Reaxys

O S

O I O S O

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O S

Rx-ID: 3818878 View in Reaxys 506/1037 Yield

Conditions & References

28 %

With copper acetylacetonate, Time= 0.25h, T= 90 °C Hatjiarapoglou, Lazaros; Varvoglis, Anastasios; Journal of Heterocyclic Chemistry; vol. 25; (1988); p. 1599 - 1600 View in Reaxys

O S

O I O S O

O S

S O

Rx-ID: 3818879 View in Reaxys 507/1037 Yield

Conditions & References

15 %

With copper acetylacetonate in chloroform, Time= 1h, Heating Hatjiarapoglou, Lazaros; Varvoglis, Anastasios; Journal of Heterocyclic Chemistry; vol. 25; (1988); p. 1599 - 1600 View in Reaxys

O I O

S O

Rx-ID: 3855158 View in Reaxys 508/1037 Yield 31 %

Conditions & References in acetonitrile, Time= 4h, Irradiation, further alkenes and alkynes;, Product distribution, Mechanism

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in acetonitrile, Time= 4h, Irradiation Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys

Rx-ID: 3857428 View in Reaxys 509/1037 Yield

Rx-ID: 3857616 View in Reaxys 510/1037 Yield 92 %

Conditions & References With iodosylbenzene, boron trifluoride diethyl etherate in dichloromethane, Time= 3h, Ambient temperature Lee, Kilsung; Kim, Dae Young; Oh, Dong Young; Tetrahedron Letters; vol. 29; nb. 6; (1988); p. 667 - 668 View in Reaxys

Rx-ID: 3857622 View in Reaxys 511/1037 Yield

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Rx-ID: 3858622 View in Reaxys 512/1037 Yield

Conditions & References

75 %

With iodosylbenzene, boron trifluoride diethyl etherate in dichloromethane, Time= 3h, T= 0 °C Lee, Kilsung; Kim, Dae Young; Oh, Dong Young; Tetrahedron Letters; vol. 29; nb. 6; (1988); p. 667 - 668 View in Reaxys

O S

O I

O S

Rx-ID: 3914139 View in Reaxys 513/1037 Yield 25 %

Conditions & References in acetonitrile, Time= 1h, Irradiation Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys

O N

Rx-ID: 3918713 View in Reaxys 514/1037 Yield 94 % Chromat.

Conditions & References With ammonium nitrate, potassium iodide in trifluoroacetic acid, Time= 0.5h, T= 20 °C , Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 11; (1988); p. 2029 - 2035; Zhurnal Organicheskoi Khimii; vol. 24; nb. 11; (1988); p. 2251 - 2258 View in Reaxys

O I

Rx-ID: 3918714 View in Reaxys 515/1037 Yield 3 % Chromat.

Conditions & References With sodium nitrate, potassium iodide in water, trifluoroacetic acid, Time= 24h, T= 20 °C , Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 11; (1988); p. 2029 - 2035; Zhurnal Organicheskoi Khimii; vol. 24; nb. 11; (1988); p. 2251 - 2258 View in Reaxys

(TPP)Cr(V)(O)(Cl)

Rx-ID: 7458477 View in Reaxys 516/1037

182/330

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Yield

Conditions & References With chloro(5,10,15,20-tetraphenylporphyrinato)chromium(III) in dichloromethane, T= 25 °C , oxygen transfer to (TPP)Cr(III) (Cl), Mechanism Lee, William A.; Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 110; nb. 13; (1988); p. 4277 - 4283 View in Reaxys

O O I

copper-powder

Rx-ID: 20130099 View in Reaxys 517/1037 Yield

Conditions & References Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 15 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h 2: acetonitrile / 6.5 h / Irradiation With potassium hydroxide in acetonitrile Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 15 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h 2: acetonitrile / 1.2 h / Irradiation With potassium hydroxide in acetonitrile Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 15 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h 2: Cu(acac)2 / 2-methyl-propan-2-ol / 5 h / Heating With potassium hydroxide, copper acetylacetonate in tert-butyl alcohol Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 15 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h 2: acetonitrile / 1 h / Irradiation With potassium hydroxide in acetonitrile Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 60 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h 2: Cu(acac)2 / 2-methyl-propan-2-ol / 5 h / Heating With potassium hydroxide, copper acetylacetonate in tert-butyl alcohol Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 60 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h

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2: Cu(acac)2 / 2-methyl-propan-2-ol / 5 h / Heating With potassium hydroxide, copper acetylacetonate in tert-butyl alcohol Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys Reaction Steps: 2 1: 1.) KOH / 1.) MeOH, -10 deg C, 15 min; 2.) MeOH, -5 deg C, 30 min, -10 deg C, 12 h 2: Cu(acac)2 / 2-methyl-propan-2-ol / 5 h / Heating With potassium hydroxide, copper acetylacetonate in tert-butyl alcohol Hatjiarapoglou, Lazaros; Varvoglis, Anastassios; Alcock, Nathaniel W.; Pike, Graham A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2839 - 2846 View in Reaxys I

Sn Sn Sn S S S

I I

Rx-ID: 26416359 View in Reaxys 518/1037 Yield

Conditions & References

With iodine in chloroform-d1, monitored by NMR Gallant, Michel; Kobayashi, Michio; Latour, Stephan; Wuest, James D.; Organometallics; vol. 7; (1988); p. 736 - 739 ; (from Gmelin) View in Reaxys

Cl O

– (v4) RuO N

(v4)

K+

(v6)

O (v4)

(v4) (v7) O

Rx-ID: 26502577 View in Reaxys 519/1037 Yield

Conditions & References

55-60

in 1,4-dioxane, water, N,N-dimethyl-formamide, in 1:1 water-dioxane/DMF, addn. of iodosylbenzene, stirred for 6 h; extn. of iodobenzene (diethyl ether), evapd. almost to dryness, addn. of ether; elem. anal. Khan, M. M. Taqui; Sreelatha, Ch.; Mirza, Shaukat A.; Ramachandraiah, G.; Abdi, S. H. R.; Inorganica Chimica Acta; vol. 154; (1988); p. 103 - 108 ; (from Gmelin) View in Reaxys Cl

(v4)

O (v4)

N O (v4)

Ru (v4)O (v6) N

(v4)

N Ru + (v4)O (v7)

Cl –

N NH

Rx-ID: 26502578 View in Reaxys 520/1037 Yield 55-60

Conditions & References in 1,4-dioxane, water, N,N-dimethyl-formamide, in 1:1 water-dioxane/DMF, addn. of iodosylbenzene, stirred for 6 h; extn. of iodobenzene (diethyl ether), evapd. almost to dryness, addn. of ether; elem. anal. Khan, M. M. Taqui; Sreelatha, Ch.; Mirza, Shaukat A.; Ramachandraiah, G.; Abdi, S. H. R.; Inorganica Chimica Acta; vol. 154; (1988); p. 103 - 108 ; (from Gmelin) View in Reaxys

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Cl (v4)

(v4)

N O (v4)

Ru (v4)O

(v6)

(v4)

N Ru + (v4)O (v7)

Cl –

N NH

Rx-ID: 26502580 View in Reaxys 521/1037 Yield

Conditions & References

55-60

N N

(v8)4

W 4N

(v4)

(v2)

C+

N W 3-

(v8)3

N N

(v4)

C+

(v2)

Rx-ID: 26526757 View in Reaxys 522/1037 Yield

Conditions & References With diphenyliodonium chloride in methanol, Irradiation (UV/VIS); 200 W xenon lamp, 0.01 M diphenyliodonium chloride, 0.001 M diphenyliodonium-cyanometallate Billing, R.; Rehorek, D.; Salvetter, J.; Henning, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 557; (1988); p. 234 - 240 ; (from Gmelin) View in Reaxys N

N N

N Mn3- N O3 (v3) (v4) (v6)

C+

(v2)

(v4)

N Mn2- N O2 (v3) (v4) (v6)

C+

(v2)

(v4)

Rx-ID: 26526952 View in Reaxys 523/1037 Yield

Conditions & References With diphenyliodonium chloride in methanol, Irradiation (UV/VIS); 200 W xenon lamp, 0.01 M diphenyliodonium chloride, 0.001 M diphenyliodoniumcyanometallate Billing, R.; Rehorek, D.; Salvetter, J.; Henning, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 557; (1988); p. 234 - 240 ; (from Gmelin) View in Reaxys N

Ru 4-

(v6)

(v4)

C+

I (v2)

Ru 3(v6)

(v4)

C+

(v2)

Rx-ID: 26527528 View in Reaxys 524/1037 Yield

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View in Reaxys With diphenyliodonium chloride in N,N-dimethyl-formamide, Irradiation (UV/VIS); 200 W xenon lamp, 0.01 M diphenyliodonium chloride, 0.001 M diphenyliodoniumcyanometallate Billing, R.; Rehorek, D.; Salvetter, J.; Henning, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 557; (1988); p. 234 - 240 ; (from Gmelin) View in Reaxys

N N

(v8)4

(v4)

C+

(v2)

N Mo3-

N N

N Mo4-

N N

(v8)3

(v4)

C+

(v2)

Rx-ID: 26527889 View in Reaxys 525/1037 Yield

Conditions & References With diphenyliodonium chloride in dichloromethane, Irradiation (UV/VIS); 200 W xenon lamp, 0.01 M diphenyliodonium chloride, 0.001 M diphenyliodoniumcyanometallate Billing, R.; Rehorek, D.; Salvetter, J.; Henning, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 557; (1988); p. 234 - 240 ; (from Gmelin) View in Reaxys With diphenyliodonium chloride in methanol, Irradiation (UV/VIS); 200 W xenon lamp, 0.01 M diphenyliodonium chloride, 0.001 M diphenyliodoniumcyanometallate Billing, R.; Rehorek, D.; Salvetter, J.; Henning, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 557; (1988); p. 234 - 240 ; (from Gmelin) View in Reaxys With diphenyliodonium chloride in N,N-dimethyl-formamide, Irradiation (UV/VIS); 200 W xenon lamp, 0.01 M diphenyliodonium chloride, 0.001 M diphenyliodoniumcyanometallate Billing, R.; Rehorek, D.; Salvetter, J.; Henning, H.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 557; (1988); p. 234 - 240 ; (from Gmelin) View in Reaxys

(v3)

(v4)

C+

5 N–

(v3)

(v2)

Fe 2+

(v3)

5 N–

(v3)

I 2

(v4)

C+

(v2)

Fe 3+

Rx-ID: 26528566 View in Reaxys 526/1037 Yield

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I+ Cl –

Rx-ID: 532738 View in Reaxys 527/1037 Yield

Conditions & References

1.2 %

in water, Irradiation, laser flash photolyses, δ: 313 nm, Product distribution Devoe, R. J.; Sahyun, M. R. V.; Serpone, N.; Sharma, D. K.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2342 - 2349 View in Reaxys T= 230 °C Hartmann; Meyer,V.; Chemische Berichte; vol. 27; (1894); p. 505 Anm. View in Reaxys T= 190 °C , Product distribution Gyoeryova, K.; Mohai, B.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 107; (1981); p. 67 - 76 View in Reaxys

N I

Rx-ID: 1496406 View in Reaxys 528/1037 Yield 14 % Chromat., 14 % Chromat.

Conditions & References With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: Pt electrode vs. Ag/Ag+ Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys

Rx-ID: 1579919 View in Reaxys 529/1037 Yield 4.82 %, 1.90 %, 3.22 %, 0.44 %

Conditions & References With sodium chloride, teflon in water, acetonitrile, Time= 0.0333333h, Irradiation Selavka; Krull; Analytical chemistry; vol. 59; nb. 22; (1987); p. 2704 - 2709 View in Reaxys

NH O

F F

Li O–

Rx-ID: 1673895 View in Reaxys 530/1037 Yield 71 %

Conditions & References With boron trifluoride diethyl etherate in tetrahydrofuran, Time= 0.25h, T= -78 °C

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Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys

O O O

I O

O O

Rx-ID: 1784015 View in Reaxys 531/1037 Yield

Conditions & References With perchloric acid in acetic acid, T= 35 °C , various concentrations of acids; ΔE(excit.), ΔH(excit.), ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Radhakrishnamurti, P. S.; Panda, H. P.; Pradhan, D. C.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 4; (1987); p. 297 - 300 View in Reaxys

O S

S+

–O

S O

Rx-ID: 1845799 View in Reaxys 532/1037 Yield

Conditions & References

99 %

in dichloromethane, Time= 0.25h Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys

O +I

–

NH O O H N S+

O –O

S O

Rx-ID: 1845850 View in Reaxys 533/1037 Yield

Conditions & References

67 %

in dichloromethane, Time= 0.5h, Ambient temperature Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys O O I+

–O

N H

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O O –O

S S+

Rx-ID: 1845851 View in Reaxys 534/1037 Yield

Conditions & References

73 %

in dichloromethane, Time= 0.5h, Ambient temperature Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys O O I+

–O

N H

S O

O O –O

S S+

Rx-ID: 1845852 View in Reaxys 535/1037 Yield

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature, Yield given Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys

O –O

H N

I+

H N

O S+

–O

S O O

Rx-ID: 1845853 View in Reaxys 536/1037 Yield 69 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys

O S

S+

–

S O O

Rx-ID: 1880094 View in Reaxys 537/1037

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Yield

Conditions & References in dichloromethane, Time= 0.25h, Yield given Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys O O O

I O

Rx-ID: 1968974 View in Reaxys 538/1037 Yield

Conditions & References With perchloric acid in acetic acid, T= 60 °C , various concentrations of acids; ΔE(excit.), ΔH(excit.), ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Radhakrishnamurti, P. S.; Panda, H. P.; Pradhan, D. C.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 4; (1987); p. 297 - 300 View in Reaxys

O O

I O

O O O

Rx-ID: 1994906 View in Reaxys 539/1037 Yield

O O O

I O

O O

Rx-ID: 1994913 View in Reaxys 540/1037 Yield

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I S

S O

O –O

S+

Rx-ID: 2015314 View in Reaxys 541/1037 Yield

Conditions & References

99 %

in dichloromethane, Time= 0.25h Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys

O +I

–

S NH O O

O S+

–O

S NH O O

Rx-ID: 2015316 View in Reaxys 542/1037 Yield

Conditions & References

72 %

in dichloromethane, Time= 0.5h, Ambient temperature Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys

O S

O S+

–O

S O O

Rx-ID: 2021698 View in Reaxys 543/1037 Yield

Conditions & References

99 %

in dichloromethane, Time= 0.25h Koser, Gerald F.; Kokil, Pandurang B.; Shah, Mayur; Tetrahedron Letters; vol. 28; nb. 45; (1987); p. 5431 - 5434 View in Reaxys

O –O

I+

Rx-ID: 2245778 View in Reaxys 544/1037

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Yield

Conditions & References

37 %

With silver trifluoromethanesulfonate in acetonitrile, Time= 20h, T= 25 °C Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

I+

–O

Rx-ID: 2245851 View in Reaxys 545/1037 Yield

Conditions & References

72 %

With silver(I) 4-methylbenzenesulfonate in acetonitrile, Time= 4h, T= 25 °C Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

I+

–O

Rx-ID: 2245980 View in Reaxys 546/1037 Yield

Conditions & References With copper(I) triflate in acetonitrile, Time= 4h, T= 25 °C Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

NH O

F F

O–

I +I

Rx-ID: 2247829 View in Reaxys 547/1037 Yield

Conditions & References

66 %

With boron trifluoride diethyl etherate in tetrahydrofuran, Time= 0.25h, T= -78 °C Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys I+ O

–O

S O

O O

I O

Rx-ID: 2314298 View in Reaxys 548/1037 Yield 88 %

Conditions & References With copper(I) triflate in acetonitrile, Time= 2h, T= 25 °C

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Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

NH O

I +I

O–

Rx-ID: 2316139 View in Reaxys 549/1037 Yield

Conditions & References

61 %

I+ I–

Rx-ID: 2428809 View in Reaxys 550/1037 Yield

Conditions & References in water, Irradiation, laser flash photolyses, δ: 355 nm, Product distribution, Mechanism Devoe, R. J.; Sahyun, M. R. V.; Serpone, N.; Sharma, D. K.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2342 - 2349 View in Reaxys -1 I+

F F

F (v6)

P F

Rx-ID: 2519523 View in Reaxys 551/1037 Yield

Conditions & References

26.5 %

in water, acetonitrile, Irradiation, laser flash photolyses, δ: 313 nm, Product distribution, Mechanism Devoe, R. J.; Sahyun, M. R. V.; Serpone, N.; Sharma, D. K.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2342 - 2349 View in Reaxys -1

F (v4)

B FF

I I

N+ N

Rx-ID: 2744683 View in Reaxys 552/1037 Yield

Conditions & References

36.6 % Chromat., 32.5 % Chromat.

With 18-crown-6 ether, 1,2-dichloro-ethane, T= 50 °C , Rate constant Nakazumi, Hiroyuki; Kitao, Teijiro; Zollinger, Heinrich; Journal of Organic Chemistry; vol. 52; nb. 13; (1987); p. 2825 2830 View in Reaxys O

I+

O –O

I O

Rx-ID: 2784456 View in Reaxys 553/1037

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Yield

Conditions & References

38 %

With copper(I) triflate in acetonitrile, Time= 2h, T= 25 °C Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys With copper(I) triflate in acetonitrile, Time= 2h, T= 25 °C , reactions of iodonium sulfonates catalytic amounts of var. of metal systems<CuOTf, AgOTf, AgOTs,(Ph3P)4Pd>crossover experiment with 23b, Product distribution, Mechanism Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

N HN

N N

Rx-ID: 2837735 View in Reaxys 554/1037 Yield

Conditions & References With tertamethylammonium iodide, trifluoroacetic acid in acetonitrile, T= 70 - 80 °C Butler, Richard N.; O'Shea, Paul D.; Shelly, Declan P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 1039 - 1042 View in Reaxys

I N

Rx-ID: 2900833 View in Reaxys 555/1037 Yield

Conditions & References

32 %, 12 %

in acetonitrile, Time= 1.66667h, Irradiation Kotali, Elvira; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 2759 - 2764 View in Reaxys

S I N

I N

S S

Rx-ID: 2900834 View in Reaxys 556/1037

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Yield

Conditions & References

77 %, 15 mg

in pyridine, Time= 24h, Ambient temperature Kotali, Elvira; Varvoglis, Anastassios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 2759 - 2764 View in Reaxys

NH F

O–

Li +I

Rx-ID: 2925593 View in Reaxys 557/1037 Yield

Conditions & References

62 %

With boron trifluoride diethyl etherate in tetrahydrofuran, T= -78 °C Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys

O–

I+

S O

Rx-ID: 3282114 View in Reaxys 558/1037 Yield

Conditions & References

60 %

With copper(I) triflate in acetonitrile, Time= 6h, T= 25 °C Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

I+ O–

Rx-ID: 3282777 View in Reaxys 559/1037 Yield

Conditions & References

50 %

With copper(I) triflate in acetonitrile, Time= 18h, Heating Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys I+ O–

S O

Rx-ID: 3282865 View in Reaxys 560/1037 Yield 54 %

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O O O

I O

Rx-ID: 3361897 View in Reaxys 561/1037 Yield

H 2N

Rx-ID: 3377171 View in Reaxys 562/1037 Yield

Conditions & References With hydrogenchloride, potassium iodide, sodium nitrite, 1.) water, poly(ethylene glycol), CH2Cl2, 0 deg C; 2.) poly(ethylene glycol), CH2Cl2, from 0 deg C to RT, Yield given. Multistep reaction. Yields of byproduct given Suzuki, Nobutaka; Azuma, Terukazu; Kaneko, Yoshihiro; Izawa, Yasuji; Tomioka, Hideo; Nomoto, Tateo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 645 - 648 View in Reaxys F F

F F F F

F F F

F F

O SO

F F

O F

I O O

F S O

F F

Rx-ID: 3494398 View in Reaxys 563/1037 Yield

Conditions & References

90 %

T= 140 - 145 °C Umemoto, Teruo; Gotoh, Yoshihiko; Bulletin of the Chemical Society of Japan; vol. 60; nb. 9; (1987); p. 3307 - 3314 View in Reaxys

O O O

I O

O O O

Rx-ID: 3536989 View in Reaxys 564/1037

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Yield

Conditions & References With perchloric acid in acetic acid, T= 60 °C , various concentrations of reagent; ΔE(excit.), ΔH(excit.), ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Radhakrishnamurti, P. S.; Panda, H. P.; Pradhan, D. C.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 4; (1987); p. 297 - 300 View in Reaxys -1 I+

F F (v6)

H N

F N

F F

Rx-ID: 3738452 View in Reaxys 565/1037 Yield

Conditions & References

3.3 %, 31 % With 3'-(trifluoromethyl)acetophenone, Irradiation, laser flash photolyses; δ: 313 nm, without sensitizer, Product distribution Devoe, R. J.; Sahyun, M. R. V.; Serpone, N.; Sharma, D. K.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2342 - 2349 View in Reaxys

Br–

+Mg

Rx-ID: 7062821 View in Reaxys 566/1037 Yield 23 %, 46 %

Conditions & References With copper(l) iodide in tetrahydrofuran, -8 deg C, 1 hr.; r.t. 30 min.; reflux 30 min., Product distribution Rahman, Mohammed T.; Nahar, Syeda K.; Journal of Organometallic Chemistry; vol. 329; nb. 1; (1987); p. 133 - 138 View in Reaxys

sulfur

m-toluic acid phenyl ester

Rx-ID: 18337081 View in Reaxys 567/1037 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / various solvent(s) / 24 h / 0 °C 2: 89 percent / 140 - 145 °C in various solvent(s) Umemoto, Teruo; Gotoh, Yoshihiko; Bulletin of the Chemical Society of Japan; vol. 60; nb. 9; (1987); p. 3307 - 3314 View in Reaxys

N–

I +I

Rx-ID: 21483319 View in Reaxys 568/1037 Yield

Conditions & References Reaction Steps: 2 1: CF3CO2H 2: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C With boron trifluoride diethyl etherate, trifluoroacetic acid in tetrahydrofuran

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Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys Reaction Steps: 2 1: CF3CO2H 2: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C With boron trifluoride diethyl etherate, trifluoroacetic acid in tetrahydrofuran Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys Reaction Steps: 2 1: CF3CO2H 2: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C With boron trifluoride diethyl etherate, trifluoroacetic acid in tetrahydrofuran Moriarty, Robert M.; Ku, Y. Y.; Sultana, M.; Tuncay, Atilla; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3071 - 3074 View in Reaxys

H (v6) (v6) H H HB B HB BBH (v6) (v6) (v6) (v6) (v6) (v6) (v6) (v6) HBB BBH H I B H (v6) H (v6)

(v6)(v6)

H (v6) F (v6) B BH (v6) HB BH HB (v6) HB BH B– (v6) + FF I B BB (v6) (v6) (v2) H H (v6) (v6)

(v6) H (v6) H HB B BH HB BH (v6) (v6) (v6) (v6) B B H H B H HOB B H (v6) H (v6)

(v6) (v6)(v6)

(v6)

(v6) H (v6) (v6)B BH HB HB BH (v6) (v6) HB (v6) BH B B (v6) ON (v6) BH O H (v6)

(v6)

Rx-ID: 26760185 View in Reaxys 569/1037 Yield

Conditions & References

7 %, 79 %, 6 %, 4 %

With sodium nitrite in dichloromethane, water, mixt. of NaNO2 and the boron contg. salt in a two phase system stirred vigorously at 40°C, 3h (accompanied by evolution of nitrogen oxides), further product: C6H5NO2 (4percent); organic layer sepd. from aq. layer, evapn. of CH2Cl2 in vac., residue sepd. by chromy. (silica gel, hexane (9-iodo-m-carbaborane); benzene-hexane 1:1 (9-nitro-m-carbaborane); ether (9-hydroxy-m-carbaborane) Demkina, I. I.; Grushin, V. V.; Vanchikov, A. N.; Tolstaya, T. P.; Orlinkov, A. V.; Journal of General Chemistry USSR (English Translation); vol. 57; (1987); p. 1199 - 1205; Zhurnal Obshchei Khimii; vol. 57; (1987); p. 1341 - 1347 ; (from Gmelin) View in Reaxys

HO O

I S

Rx-ID: 46745653 View in Reaxys 570/1037 Yield

Conditions & References Reaction Steps: 2 1: dichloromethane / 8 h / Ambient temperature 2: copper(I) triflate / acetonitrile / 4 h / 25 °C With copper(I) triflate in dichloromethane, acetonitrile Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys Reaction Steps: 2 1: dichloromethane / 96 h / Ambient temperature 2: copper(I) triflate / acetonitrile / 18 h / Heating With copper(I) triflate in dichloromethane, acetonitrile Stang,P.J.; Surber,B.W.; Chen,Z.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 228 View in Reaxys

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Rx-ID: 421691 View in Reaxys 571/1037 Yield

Conditions & References With tetrachloromethane, iodine Bost; Borgstrom; Journal of the American Chemical Society; vol. 51; (1929); p. 1924 View in Reaxys With tetrachloromethane, Iodine monochloride Bost; Borgstrom; Journal of the American Chemical Society; vol. 51; (1929); p. 1924 View in Reaxys 20 : EXAMPLE 20 In control runs 1, 2 and 3 iodobenzene was precipitated by decomposition of tetraphenyl tin or triphenyl phosphine. Patent; Mitsubishi Gas Chemical Company, Inc.; US4620033; (1986); (A) English View in Reaxys O

O S

H 2N

S O

Rx-ID: 1729828 View in Reaxys 572/1037 Yield 17 %, 80 %

Conditions & References With <(tosylimido)iodo>benzene, Fe(III) tetraarylporphyrin in dichloromethane, the intermediate Fe-complex was investigated Mahy, Jean-Pierre; Battioni, Pierrette; Mansuy, Daniel; Journal of the American Chemical Society; vol. 108; nb. 5; (1986); p. 1079 - 1080 View in Reaxys

O –O

O–

I+

O S O O

I O

Rx-ID: 1985961 View in Reaxys 573/1037 Yield

Conditions & References in dichloromethane Stang,P.J.; Boeshar,M.; Lin,J.; Journal of the American Chemical Society; vol. 108; (1986); p. 7832 View in Reaxys

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I+

O –O

–

I O

Rx-ID: 1985962 View in Reaxys 574/1037 Yield

Conditions & References in dichloromethane Stang,P.J.; Boeshar,M.; Lin,J.; Journal of the American Chemical Society; vol. 108; (1986); p. 7832 View in Reaxys

H C

Rx-ID: 2011222 View in Reaxys 575/1037 Yield 17 %, 2 %

Conditions & References With tri-n-butyl-tin hydride, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, T= 50 °C , investigation the effect of varying the reaction conditions (quantity of Bu3SnH), Product distribution Baillargeon,V.P.; Stille,J.K.; Journal of the American Chemical Society; vol. 108; (1986); p. 452 View in Reaxys

O O

I O

O Cl Cl

I O

Cl Cl

Cl O

Cl Cl

Rx-ID: 2099678 View in Reaxys 576/1037 Yield 43 %

Conditions & References in dichloromethane, Time= 6h, Ambient temperature Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

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O I O

O Cl

Cl Cl

Cl O

O Cl

O O

Cl Cl

Rx-ID: 2099679 View in Reaxys 577/1037 Yield

Conditions & References

15 %, 15 %, Time= 0.05h, T= 200 °C , Heating 64 % Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

O Cl

I O

Cl Cl

Rx-ID: 2099680 View in Reaxys 578/1037 Yield 40 %

Conditions & References With iodine in dichloromethane, Time= 6h, Heating Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

Cl As Cl

Rx-ID: 2184573 View in Reaxys 579/1037

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Yield

Conditions & References

70 %

With Iodine monochloride in acetonitrile, Time= 0.5h, T= 0 °C Raizada, Meenu Singh; Nigam, H. L.; Journal of the Indian Chemical Society; vol. 63; (1986); p. 722 - 724 View in Reaxys

Rx-ID: 2184574 View in Reaxys 580/1037 Yield

Conditions & References With iodine in acetonitrile, Heating Raizada, Meenu Singh; Nigam, H. L.; Journal of the Indian Chemical Society; vol. 63; (1986); p. 722 - 724 View in Reaxys

O O

I O

Cl O

O O

O Cl

Rx-ID: 2203592 View in Reaxys 581/1037 Yield 75 %

202/330

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O O

I O

O Br

I O

Cl O

O Cl

Rx-ID: 2203594 View in Reaxys 582/1037 Yield

Conditions & References

47 %

in dichloromethane, Time= 6h, Ambient temperature Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

Cl O

I O

O O

O Cl Cl O

O Cl

Rx-ID: 2203595 View in Reaxys 583/1037 Yield 54 %

203/330

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I+

O–

O –O

P O

O S

O O

I P O

Rx-ID: 2216788 View in Reaxys 584/1037 Yield

Conditions & References in dichloromethane, Ambient temperature, Yield given Stang,P.J.; Boeshar,M.; Lin,J.; Journal of the American Chemical Society; vol. 108; (1986); p. 7832 View in Reaxys

I+

O –O

O O

S O–

O O O

I O

Rx-ID: 2245767 View in Reaxys 585/1037 Yield

Conditions & References in dichloromethane Stang,P.J.; Boeshar,M.; Lin,J.; Journal of the American Chemical Society; vol. 108; (1986); p. 7832 View in Reaxys

I+ O

O –O

S O–

O O

I O

Rx-ID: 2245849 View in Reaxys 586/1037 Yield

Conditions & References in dichloromethane Stang,P.J.; Boeshar,M.; Lin,J.; Journal of the American Chemical Society; vol. 108; (1986); p. 7832 View in Reaxys

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F F

O F

S O

O F

F F

Rx-ID: 2635837 View in Reaxys 587/1037 Yield

Conditions & References

73 %

Time= 0.5h, T= 145 - 151 °C , p= 0.1 - 0.2Torr Umemoto, Teruo; Kuriu, Yuriko; Shuyama, Hideo; Miyano, Osamu; Nakayama, Shin-Ichi; Journal of Fluorine Chemistry; vol. 31; nb. 1; (1986); p. 37 - 56 View in Reaxys

O O O

I O

O O

Rx-ID: 2997302 View in Reaxys 588/1037 Yield 33 %

O O I O

205/330

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O O

Rx-ID: 3000610 View in Reaxys 589/1037 Yield 29 %

O O I O

O Br

HO O

Br O

O Br

Rx-ID: 3004718 View in Reaxys 590/1037 Yield 21 %, 8 %, 49 %

Conditions & References Time= 0.5h, T= 200 °C Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

20 %, 58 %

in various solvent(s), Time= 0.5h, T= 174 °C , Heating Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

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O Br

I O

Rx-ID: 3004719 View in Reaxys 591/1037 Yield 50 %

Conditions & References With iodine in benzene, Time= 6h, Heating Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

O O I O

O O

Rx-ID: 3006888 View in Reaxys 592/1037 Yield 25 %

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Cl O

I O

O O

Cl O

O Cl Cl O

O O

O O Cl

Rx-ID: 3021888 View in Reaxys 593/1037 Yield

Conditions & References

10 %

With iodine in dichloromethane, Time= 6h, Heating Menkisoglou-Spyroudi, Ourania; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 795 - 798 View in Reaxys

I+ O–

Rx-ID: 3495113 View in Reaxys 594/1037 Yield

Conditions & References in dichloromethane, Ambient temperature, Yield given Stang,P.J.; Boeshar,M.; Lin,J.; Journal of the American Chemical Society; vol. 108; (1986); p. 7832 View in Reaxys

O Sn

Rx-ID: 4020484 View in Reaxys 595/1037 Yield

Conditions & References With iodine in methanol, T= 25 °C Ravenscroft, M. D.; Roberts, R. M. G.; Journal of Organometallic Chemistry; vol. 312; (1986); p. 45 - 52 View in Reaxys

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(v1) I–

C–

(v5)

(v4) 3+(v5) N Rh N – – N (v4) N (v3) (v3) (v4)

3+ N Rh N – – N (v4) N(v3) (v3)

(v4)

Rx-ID: 26976790 View in Reaxys 596/1037 Yield

Conditions & References With iodine in dichloromethane, benzene, soln. containing iodine was stirred at room temp. under N2 for 3 d; soln. was washed with aq. Na2S2O4, organic layer was dried (Na2SO4), chromd. on silica gel Aoyama, Yasuhiro; Yoshida, Tohru; Sakurai, Ken-ichi; Ogoshi, Hisanobu; Organometallics; vol. 5; (1986); p. 168 - 173 ; (from Gmelin) View in Reaxys

Rx-ID: 1917864 View in Reaxys 597/1037 Yield

Conditions & References With <bis(trifluoroacetoxy)iodo>benzene, silica gel, 1) CHCl3/CH3CN/H2O, 80 deg C, 5 h, 2) ethyl acetate, Yield given. Multistep reaction Tamura, Yasumitsu; Yakura, Takayuki; Haruta, Jun-ichi; Kita, Yasuyuki; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3837 - 3840 View in Reaxys OH

I HO O

Rx-ID: 1944392 View in Reaxys 598/1037 Yield

Conditions & References With <bis(trifluoroacetoxy)iodo>benzene, silica gel, 1) CHCl3/CH3CN/H2O, 80 deg C, 10 h, 2) ethyl acetate, Yield given. Multistep reaction Tamura, Yasumitsu; Yakura, Takayuki; Haruta, Jun-ichi; Kita, Yasuyuki; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3837 - 3840 View in Reaxys Cl Cl Cl Cl

Cl Cl

Rx-ID: 1980158 View in Reaxys 599/1037 Yield 98 % Chromat.

Conditions & References in chloroform, Time= 4h, T= 60 °C Saginova, L. G.; Bondarenko, O. B.; Gazzaeva, R. A.; Shabarov, Yu. S.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 3; (1985); p. 477 - 480; Zhurnal Organicheskoi Khimii; vol. 21; nb. 3; (1985); p. 526 - 530 View in Reaxys

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Cl Cl Cl

Cl Cl

O O O

I O

Cl Cl

Rx-ID: 2007634 View in Reaxys 600/1037 Yield 95 % Chromat.

I O

Rx-ID: 2032273 View in Reaxys 601/1037 Yield

Conditions & References With phosphate buffer, Anthracen-9,10-bisaethansulfonsaeure, dihydrogen peroxide in water, T= 25 °C , pH 2.74; other pH-s, Product distribution, Rate constant, Mechanism Evans, Dennis F.; Upton, Mark W.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1985); p. 1141 - 1145 View in Reaxys Cl Cl Cl O O O

I O

Cl Cl

Cl Cl Cl

Cl O Cl

Rx-ID: 2063912 View in Reaxys 602/1037 Yield 97 % Chromat.

210/330

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O– I+

Rx-ID: 2083111 View in Reaxys 603/1037 Yield

Conditions & References

22 %

Time= 2h, T= 200 °C Miller, Robert D.; Franz, Lothar; Fickes, Garry N.; Journal of Organic Chemistry; vol. 50; nb. 17; (1985); p. 3200 - 3203 View in Reaxys O

O S O

Rx-ID: 2109015 View in Reaxys 604/1037 Yield

Conditions & References With dodecyltributylphosphonium iodide, T= 100 °C Fry, Slaton R.; Pienta, Norbert J.; Journal of the American Chemical Society; vol. 107; nb. 22; (1985); p. 6399 - 6400 View in Reaxys With dodecyltributylphosphonium iodide, T= 100 °C , in molten phosphonium iodide, Rate constant Fry, Slaton R.; Pienta, Norbert J.; Journal of the American Chemical Society; vol. 107; nb. 22; (1985); p. 6399 - 6400 View in Reaxys

I+

C–

Cl –

O O

Rx-ID: 2225046 View in Reaxys 605/1037 Yield

Conditions & References With dimethyl sulfoxide, T= 25 °C , Rate constant Bordwell, Frederick G.; Clemens, Anthony H.; Smith, Donald E.; Begemann, John; Journal of Organic Chemistry; vol. 50; nb. 8; (1985); p. 1151 - 1156 View in Reaxys

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I+

S Cl –

C– Br

S I

Rx-ID: 2229776 View in Reaxys 606/1037 Yield

I+ Cl –

C– Br

I O

Rx-ID: 2241017 View in Reaxys 607/1037 Yield

I+

S Cl –

C– Br

212/330

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Br S

Rx-ID: 2241021 View in Reaxys 608/1037 Yield

I+ Br–

(v2)

Rx-ID: 2429606 View in Reaxys 609/1037 Yield 77 %, 8 %, 9 %, 75 %

Conditions & References With tetramethylammonium perchlorate in N,N-dimethyl-formamide, electrolytic reduction at mercury pool cathode; various potentials (various coulometric n values); other unsymmetrically substituted diphenyliodonium bromides, Product distribution, Mechanism Mubarak, Mohammad S.; Peters, Dennis G.; Journal of Organic Chemistry; vol. 50; nb. 5; (1985); p. 673 - 677 View in Reaxys

(v2) I–

Li+

Rx-ID: 2502338 View in Reaxys 610/1037 Yield

Conditions & References With 1-iodo-butane in tetrahydrofuran, T= -78 °C , solvent effect, Equilibrium constant Reich, Hans J.; Phillips, Nancy H.; Reich, Ieve L.; Journal of the American Chemical Society; vol. 107; nb. 13; (1985); p. 4101 - 4103 View in Reaxys I

Br– I

+Mg

Rx-ID: 2536195 View in Reaxys 611/1037 Yield

Conditions & References With iodide, 1.) THF, RT, 2 h, 2) THF, 10 deg C, 1 h, Yield given. Multistep reaction. Yields of byproduct given Hart, Harold; Harada, Katsumasa; Du, Chi-Jen Frank; Journal of Organic Chemistry; vol. 50; nb. 17; (1985); p. 3104 - 3110 View in Reaxys

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Rx-ID: 2537888 View in Reaxys 612/1037 Yield

Conditions & References With <bis(trifluoroacetoxy)iodo>benzene, silica gel, 1) CHCl3/CH3CN/H2O, 80 deg C, 12 h, 2) ethyl acetate, Yield given. Multistep reaction Tamura, Yasumitsu; Yakura, Takayuki; Haruta, Jun-ichi; Kita, Yasuyuki; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3837 - 3840 View in Reaxys O

I OH

O OH

Rx-ID: 2610297 View in Reaxys 613/1037 Yield

Conditions & References With <bis(trifluoroacetoxy)iodo>benzene, silica gel, 1) ClCH2CH2Cl/CH3CN/H2O, 100 deg C, 4 h, 2) ethyl acetate, Yield given. Multistep reaction Tamura, Yasumitsu; Yakura, Takayuki; Haruta, Jun-ichi; Kita, Yasuyuki; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3837 - 3840 View in Reaxys

I HO HO

Rx-ID: 2720746 View in Reaxys 614/1037 Yield

I GeH

Rx-ID: 2926766 View in Reaxys 615/1037 Yield 62 % Chromat., 0.7 %

Conditions & References With GeI2 in diethyl ether, Time= 120h, Ambient temperature, Ph3PGeI2, Product distribution

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Chromat., 32 % Chromat.

Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 View in Reaxys

O O

S N

S O

Rx-ID: 3266707 View in Reaxys 616/1037 Yield

Conditions & References With potassium phosphate, cytochrome P-450-LM 3,4 in glycerol, T= 30 °C , Nitrogen atom transfer, amidation product depends of ratio and conc. of isozyme mixture Svastits, Edmund W.; Dawson, John H.; Breslow, Ronald; Gellman, Samuel H.; Journal of the American Chemical Society; vol. 107; nb. 22; (1985); p. 6427 - 6428 View in Reaxys O

I HO

Rx-ID: 3365765 View in Reaxys 617/1037 Yield

Conditions & References With <bis(trifluoroacetoxy)iodo>benzene, silica gel, 1) CHCl3/CH3CN/H2O, 80 deg C, 6 h, 2) ethyl acetate, Yield given. Multistep reaction Tamura, Yasumitsu; Yakura, Takayuki; Haruta, Jun-ichi; Kita, Yasuyuki; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3837 - 3840 View in Reaxys F

F F

I F

F I

F F

O O

F F

Rx-ID: 3493941 View in Reaxys 618/1037 Yield 90 %

Conditions & References T= 140 - 145 °C Unemoto, Teruo; Gotoh, Yoshihiko; Journal of Fluorine Chemistry; vol. 28; (1985); p. 235 - 240 View in Reaxys

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O S N

Rx-ID: 3774375 View in Reaxys 619/1037 Yield

Conditions & References With 18-crown-6 ether, potassium iodide in diethyl ether, acetonitrile, Time= 4h, Ambient temperature Evers, Michel J.; Christiaens, Leon E.; Guillaume, Marcel R.; Renson, Marcel J.; Journal of Organic Chemistry; vol. 50; nb. 10; (1985); p. 1779 - 1780 View in Reaxys F F F F

F F

Rx-ID: 3779167 View in Reaxys 620/1037 Yield 96 % Chromat.

Conditions & References in chloroform, trifluoroacetic acid, Time= 4h, T= 20 °C Saginova, L. G.; Bondarenko, O. B.; Gazzaeva, R. A.; Shabarov, Yu. S.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 3; (1985); p. 477 - 480; Zhurnal Organicheskoi Khimii; vol. 21; nb. 3; (1985); p. 526 - 530 View in Reaxys F F F

F F

O O O

I O

F F

Rx-ID: 3779176 View in Reaxys 621/1037 Yield 98 % Chromat.

I O

216/330

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F F F

F O F

Rx-ID: 3779184 View in Reaxys 622/1037 Yield

Conditions & References

96 % Chromat.

in chloroform, acetone, Time= 4h, T= 20 °C Saginova, L. G.; Bondarenko, O. B.; Gazzaeva, R. A.; Shabarov, Yu. S.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 3; (1985); p. 477 - 480; Zhurnal Organicheskoi Khimii; vol. 21; nb. 3; (1985); p. 526 - 530 View in Reaxys

HO NH 2

CO2

Rx-ID: 6211663 View in Reaxys 623/1037 Yield

Conditions & References With perchloric acid, [bis(acetoxy)iodo]benzene in acetic acid, T= 60 °C , various conc. of AcOH, other temp.; other reagent; E(activ.), ΔH(excit.), lgA, ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Radhakrishamurti, P. S.; Panda, H. P.; Pradhan, D. C.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 24; nb. 7; (1985); p. 586 - 588 View in Reaxys

H O

CO2

NH 2 O

Rx-ID: 7072198 View in Reaxys 624/1037 Yield

H 2N

CO2

Rx-ID: 7072220 View in Reaxys 625/1037 Yield

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NH 2

CO2

Rx-ID: 7072244 View in Reaxys 626/1037 Yield

CO2 O

H H 2N

Rx-ID: 7452252 View in Reaxys 627/1037 Yield

dimethoxycarbonyl-δ-resorcylic acid-chloride

HNO3+H2SO4

Rx-ID: 19265065 View in Reaxys 628/1037 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / triflic acid / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 24 h / 0 °C 2: 89 percent / 140 - 145 °C With trifluorormethanesulfonic acid in 1,1,2-Trichloro-1,2,2-trifluoroethane Unemoto, Teruo; Gotoh, Yoshihiko; Journal of Fluorine Chemistry; vol. 28; (1985); p. 235 - 240 View in Reaxys

Rx-ID: 25139766 View in Reaxys 629/1037 Yield

Conditions & References 4 : EXAMPLE 4 EXAMPLE 4 The first-stage reaction was carried out by stirring a mixture of 361 g. (1 mole) of diphenyl iodonium bromide, 115 g. (1.1 mole) of styrene and 185 g. (1 mole) of the base (n-Bu)3 N in 1 l of methyl alcohol together with 0.1 g. of bis(benzylideneacetone)palladium (Pd(dba)2) catalyst at a temperature of 50° C. for a period of 6 hours. After completion of the reaction, the mixture was cooled to room temperature followed by separation of the catalyst by filtration. The methyl alcohol was removed by distillation, and the residue was subjected to distillation under reduced pressure to give 192 g. of a distillate (1) boiling at 65°-75° C. at 10 mmHg and then steam distillation to recover 171 g. of a distillate (2). IR spectra and NMR spectra indicated that the distillate (1) was iodobenzene (yield 94percent) and the distillate (2) was the desired product, stilbene (trans form) (yield 95percent).

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Patent; Nippon Petrochemicals Company, Limited; US4554360; (1985); (A) English View in Reaxys O

Rx-ID: 25147655 View in Reaxys 630/1037 Yield

Conditions & References 1 : EXAMPLE 1 EXAMPLE 1 The first-stage reaction was carried out by stirring a mixture of 361 g. (1 mole) of diphenyl iodonium bromide, 95 g. (1.1 mole) of methyl acrylate and 82 g. (1 mole) of sodium acetate in 1 l of methanol solvent together with 0.1 g. of palladium-on-active carbon catalyst at a temperature of 55° C. for a period of 4 hours. After completion of the reaction, the mixture was cooled to room temperature followed by separation of the catalyst by filtration. The methanol solvent was then removed by distillation and the reaction product was separated by distillation under reduced pressure. There were obtained 196 g. of a distillate (1) boiling at 65° C.-75° C. at 10 mmHg and 149 g. of a distillate (2) boiling at 125° C.-140° C. The distillate (1) and the distillate (2) were found by infrared absorption analysis and nuclear magnetic resonance analysis to be iodobenzene (yield 96percent) and methyl cinnamate (yield 92percent), respectively. Patent; Nippon Petrochemicals Company, Limited; US4554360; (1985); (A) English View in Reaxys C.1 : COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 The first-stage reaction was carried out in the same way as in Example 1 except that 172 g. (2 mole) of methyl acrylate and 135 g. (1.6 mol) of sodium acetate were used and the reaction time was 7 hours. Yield of iodobenzene was reduced to 46percent. Yield of the desired methyl cinnamate was over 130percent. Patent; Nippon Petrochemicals Company, Limited; US4554360; (1985); (A) English View in Reaxys

(v2)

I GeH

Rx-ID: 26590368 View in Reaxys 631/1037 Yield 62 %, 0.7 %, 32 %

Conditions & References in diethyl ether, under N2, to suspn. of GeI2 in ether PhLi (0.44 M soln. in ether) (1:4 molar ratio) added dropwise at room temp., stirred for 5 d under reflux,hydrolyzed; analyzed by gas chromy. Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 ; (from Gmelin) View in Reaxys

13 %, 0.6 %, 11 %

in diethyl ether, under N2, to suspn. of GeI2 in ether PhLi (0.44 M soln. in ether) (1:2 molar ratio) added dropwise at room temp., stirred for 5 d under reflux,hydrolyzed; analyzed by gas chromy.

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Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 ; (from Gmelin) View in Reaxys 3.8 %, 1.9 %, 1.6 %

in diethyl ether, under N2, to suspn. of GeI2 in ether PhLi (0.44 M soln. in ether) (1:1 molar ratio) added dropwise at room temp., stirred for 5 d under reflux,hydrolyzed; analyzed by gas chromy. Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 ; (from Gmelin) View in Reaxys

(v3)

(v4)

P Ge II

GeH

Rx-ID: 26970821 View in Reaxys 632/1037 Yield

Conditions & References

13 %, 39 %, in diethyl ether, under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:4 molarratio), stirred for 5 d under reflux, 36 %, 100 hydrolyzed; dried, analyzed by gas chromy. % Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 ; (from Gmelin) View in Reaxys 2.9 %, 1.9 in diethyl ether, under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:1 molarratio), stirred for 5 d under reflux, %, 14 %, 82 hydrolyzed; dried, analyzed by gas chromy. % Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 ; (from Gmelin) View in Reaxys 9.6 %, 1.3 in diethyl ether, under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:2 molarratio), stirred for 5 d under reflux, %, 19 %, 79 hydrolyzed; dried, analyzed by gas chromy. % Inoguchi, Yoshio; Okui, Shuko; Mochida, Kunio; Itai, Akiko; Bulletin of the Chemical Society of Japan; vol. 58; nb. 3; (1985); p. 974 - 977 ; (from Gmelin) View in Reaxys

O I

S O

O H 2N

S O

Rx-ID: 1545659 View in Reaxys 633/1037

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Yield 80 %, 20 %

Conditions & References With 5,10,15,20-tetraphenyl-21 H,23- H-porphine manganese(III)chloride in dichloromethane, T= 20 °C Mansuy, Daniel; Mahy, Jean-Pierre; Dureault, Annie; Bedi, Gustave; Battioni, Pierrette; Journal of the Chemical Society, Chemical Communications; nb. 17; (1984); p. 1161 - 1163 View in Reaxys

O I

S O

O O

H 2N

S O

Rx-ID: 1620953 View in Reaxys 634/1037 Yield 40 %, 56 %

O I

S O

O O

H 2N

Rx-ID: 1825272 View in Reaxys 635/1037 Yield 63 %, 37 %

Conditions & References With meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride in dichloromethane, T= 20 °C Mansuy, Daniel; Mahy, Jean-Pierre; Dureault, Annie; Bedi, Gustave; Battioni, Pierrette; Journal of the Chemical Society, Chemical Communications; nb. 17; (1984); p. 1161 - 1163 View in Reaxys

O I

S O

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O O H 2N

Rx-ID: 1825455 View in Reaxys 636/1037 Yield 65 %, 32 %

F F

F F F

F F

Rx-ID: 1846466 View in Reaxys 637/1037 Yield 83.5 %, 0.25 %

Conditions & References With dibenzoyl peroxide, T= 100 °C Brace, Neal O.; Marshall, Lawrence W.; Pinson, Carol J.; Wingerden, Gail van; Journal of Organic Chemistry; vol. 49; nb. 13; (1984); p. 2361 - 2368 View in Reaxys

Rx-ID: 1980161 View in Reaxys 638/1037 Yield 66 %

Conditions & References With [bis(acetoxy)iodo]benzene, iodine in chloroform, trifluoroacetic acid, Time= 8h, T= -30 °C Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

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O O I O

I O O

Rx-ID: 1994909 View in Reaxys 639/1037 Yield

Conditions & References With iodine in chloroform, trifluoroacetic acid, Time= 5h, T= -30 °C , Product distribution Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

O O I O

O O

I O

O O

Rx-ID: 1994910 View in Reaxys 640/1037 Yield

Conditions & References With iodine in nitromethane, Time= 1h, T= 20 °C , Product distribution Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys With iodine in tetrachloromethane, Time= 1h, T= 20 °C , Yield given. Yields of byproduct given Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

O O I O

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I O

I O O

O O

Rx-ID: 1994911 View in Reaxys 641/1037 Yield

Conditions & References With iodine in tetrachloromethane, Time= 1h, T= 20 °C , other solvent; other temperature, Product distribution Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys With iodine in tetrachloromethane, Time= 1h, T= 20 °C , Yield given. Yields of byproduct given Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

I O O

Rx-ID: 2007644 View in Reaxys 642/1037 Yield 41 %

Conditions & References With [bis(acetoxy)iodo]benzene, iodine in chloroform, trifluoroacetic acid, Time= 5h, T= -30 °C , Yields of byproduct given Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

F F O I

F OH

O F

I F

O F

F F

Rx-ID: 2007645 View in Reaxys 643/1037 Yield

Conditions & References With bis-[(trifluoroacetoxy)iodo]benzene in nitromethane, Time= 1h, T= 20 °C , Yield given. Yields of byproduct given Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

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O Cl

I Cl

Rx-ID: 2061617 View in Reaxys 644/1037 Yield

Conditions & References

64 %

in diethyl ether, T= -78 - 20 °C , argon atmosphere, Product distribution Livantsov, M. V.; Proskurnina, M. V.; Prishchenko, A. A.; Lutsenko, I. F.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 11; (1984); p. 2504 - 2517,2237 - 2249 View in Reaxys

O P

Rx-ID: 2061618 View in Reaxys 645/1037 Yield

Conditions & References

61 %

I O

Rx-ID: 2063126 View in Reaxys 646/1037 Yield

Conditions & References

50 %

With [bis(acetoxy)iodo]benzene, iodine in chloroform, trifluoroacetic acid, Time= 5h, T= -20 °C Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

Rx-ID: 2063913 View in Reaxys 647/1037 Yield

Conditions & References

54 %

With [bis(acetoxy)iodo]benzene, iodine in chloroform, trifluoroacetic acid, Time= 8h, T= -30 °C Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

O O

S I

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S O

S HO

Rx-ID: 2087026 View in Reaxys 648/1037 Yield

Conditions & References With diphenyl cadmium in diethyl ether, Time= 2h, Heating, Product distribution, Mechanism Khodair, A. I.; Abdel-Wahab, A. A.; El-Khawaga, A. M.; Schank, K.; Phosphorus and Sulfur and the Related Elements; vol. 21; (1984); p. 321 - 326 View in Reaxys

Rx-ID: 2152986 View in Reaxys 649/1037 Yield

Conditions & References

98 %

I+ Cl –

Rx-ID: 2241025 View in Reaxys 650/1037 Yield

Conditions & References With triethylamine in methanol, ethylene glycol, T= 40 °C , temp. higher than 600 deg C, Rate constant, Mechanism Skrunts, L. K.; Levit, A. F.; Kiprianova, L. A.; Gragerov, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 526 - 530; Zhurnal Organicheskoi Khimii; vol. 16; nb. 3; (1980); p. 604 - 608 View in Reaxys With δ-phenylbenzoin in water, acetonitrile, Irradiation, further initiators PhCO-C(OR1)(R2)Ph for the photoinduced decomposition; further solvents, Quantum yield Baumann, Harald; Timpe, Hans-Joachim; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 24; nb. 1; (1984); p. 18 - 19 View in Reaxys -1

F (v4)

B FF

S N

S– Na +

I+

Rx-ID: 2243636 View in Reaxys 651/1037 Yield

Conditions & References in water, 1,2-dichloro-ethane, Time= 10h, T= 72 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338

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View in Reaxys 90 % Chromat., 5 % Chromat.

in water, 1,2-dichloro-ethane, Time= 10h, T= 72 °C , other diphenylhalonium fluoroborates, other reaction time, Product distribution Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

-1 F (v4)

B FF

O S

O S– I+

Na +

Rx-ID: 2243637 View in Reaxys 652/1037 Yield

Conditions & References

99 %

in chloroform, water, Time= 64h, T= 20 °C Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

97 %

in chloroform, water, Time= 2.5h, T= 56 °C , other temperatures, other reaction time, Product distribution Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys -1

F (v4)

B FF

I+

Rx-ID: 2243659 View in Reaxys 653/1037 Yield 96 % Spectr.

Conditions & References With potassium fluoride, 18-crown-6 ether in water, 1,2-dichloro-ethane, Time= 12h, T= 80 °C , other reagent: NaF, 18-crown-6 absence, Title compound not separated from byproducts Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

96 % Spectr.

With potassium fluoride, 18-crown-6 ether in 1,2-dichloro-ethane, Time= 12h, T= 80 °C , other reagent: NaF, other solvents: chloroform-water, 1,2-dichloroethane-water, Product distribution Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

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-1 F (v4)

B FF

O N

I I+

Rx-ID: 2243661 View in Reaxys 654/1037 Yield

Conditions & References

99 % Chromat.

With sodium nitrite in chloroform, water, Time= 1.5h, T= 56 °C , Title compound not separated from byproducts Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys With sodium nitrite in chloroform, water, Time= 2.5h, T= 40 - 50 °C , also in H2O and in the presence of Et3NCH2Ph(1+)*Br(1-), Product distribution Grushin, V. V.; Tolstaya, T. P.; Lisichkina, I. N.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; (1982); p. 1925 - 1926; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1982); p. 2175 - 2176 View in Reaxys

-1 F (v4)

B FF

N N

I+

Rx-ID: 2243662 View in Reaxys 655/1037 Yield

Conditions & References

96 % Chromat.

With sodium azide in chloroform, water, Time= 0.5h, T= 56 °C , Title compound not separated from byproducts Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

96 % Chromat.

With sodium azide in chloroform, water, Time= 0.5h, T= 56 °C , other reagent: NaNO2, other reaction time, Product distribution Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

-1 F (v4)

B FF

O +I

Rx-ID: 2327623 View in Reaxys 656/1037 Yield 9 %, 90 %, 90 % Chromat.

Conditions & References With sodium nitrite in chloroform, water, Time= 3h, T= 56 °C , Title compound not separated from byproducts

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Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys 9 %, 90 %, 90 % Chromat.

With sodium nitrite in chloroform, water, Time= 3h, T= 56 °C

9 %, 90 %, 90 % Chromat.

With sodium nitrite in chloroform, water, Time= 3h, T= 56 °C , other substituted arylphenyliodonium fluoroborates, diphenyliodonium fluoroborate, other reaction time, Product distribution

Rx-ID: 2949361 View in Reaxys 657/1037 Yield

Conditions & References With trimethylsilyl iodide, isopentyl nitrite in tetrachloromethane, T= -40 °C , Yield given Weiss, Robert; Wagner, Klaus-Georg; Chemische Berichte; vol. 117; nb. 5; (1984); p. 1973 - 1976 View in Reaxys

I O

Rx-ID: 2963724 View in Reaxys 658/1037 Yield

Conditions & References With iodine, iodotriphenylstannane in N,N-dimethyl-formamide, Yield given Kashin, A. N.; Tul'chinskii, M. L.; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; nb. 8; (1984); p. 1467 - 1475; Zhurnal Organicheskoi Khimii; vol. 20; nb. 8; (1984); p. 1611 - 1620 View in Reaxys With iodine in tetrachloromethane, Yield given Kashin, A. N.; Tul'chinskii, M. L.; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; nb. 8; (1984); p. 1467 - 1475; Zhurnal Organicheskoi Khimii; vol. 20; nb. 8; (1984); p. 1611 - 1620 View in Reaxys -1

F (v4)

B FF

N O

Rx-ID: 3597339 View in Reaxys 659/1037

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Yield

Conditions & References

98 %

With sodium nitrite in chloroform, water, Time= 0.25h, T= 56 °C Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys -1

(v4)

B FF

N O

I O

O N

N O

I+

Rx-ID: 3597599 View in Reaxys 660/1037 Yield 1 %, 98 %, 1 % Chromat.

Conditions & References With sodium nitrite in chloroform, water, Time= 1h, T= 56 °C Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys F F F O O O

I O

F F

I OH

O F

I F

O F

Rx-ID: 3779173 View in Reaxys 661/1037 Yield

I O

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F F O I

F O

O F

I F

O F

F F

Rx-ID: 3779174 View in Reaxys 662/1037 Yield

I O

F F

F F O I

F OH

O F

I F

O F

F F

Rx-ID: 3779175 View in Reaxys 663/1037 Yield

Conditions & References With iodine in nitromethane, Time= 1h, T= 20 °C , Product distribution Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys With iodine in nitromethane, Time= 1h, T= 20 °C , Yield given. Yields of byproduct given Saginova. L. G.; Bondarenko, O. B.; Shabarov, Yu. S.; Gazzaev, R. A.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 1935 - 1939; Zhurnal Organicheskoi Khimii; vol. 20; nb. 10; (1984); p. 2124 - 2129 View in Reaxys

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F F F O O O

I O

F F

F F F

I O

F O F

Rx-ID: 3779180 View in Reaxys 664/1037 Yield

Conditions & References

80 %

in chloroform, trifluoroacetic acid, Time= 1h, Product distribution Gazzaeva, R. A.; Shabarov, Yu. A.; Saginova, L. G.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 199 - 200; Zhurnal Organicheskoi Khimii; vol. 20; nb. 1; (1984); p. 220 - 221 View in Reaxys

80 %

in chloroform, trifluoroacetic acid, Time= 1h Gazzaeva, R. A.; Shabarov, Yu. A.; Saginova, L. G.; Journal of Organic Chemistry USSR (English Translation); vol. 20; (1984); p. 199 - 200; Zhurnal Organicheskoi Khimii; vol. 20; nb. 1; (1984); p. 220 - 221 View in Reaxys

N F HO F

N O

CO2 HO

Rx-ID: 5728222 View in Reaxys 665/1037 Yield

Conditions & References With dibenzoyl peroxide, iron(III) in acetonitrile, T= 80 °C , Yield given Castaldi, Graziano; Minisci, Francesko; Tortelli, Vito; Vismara, Elena; Tetrahedron Letters; vol. 25; nb. 35; (1984); p. 3897 - 3900 View in Reaxys

HO F

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CO2

Rx-ID: 5728223 View in Reaxys 666/1037 Yield

N F HO F

CO2 HO

Rx-ID: 5728224 View in Reaxys 667/1037 Yield

Conditions & References With dibenzoyl peroxide in acetonitrile, T= 80 °C , Yield given Castaldi, Graziano; Minisci, Francesko; Tortelli, Vito; Vismara, Elena; Tetrahedron Letters; vol. 25; nb. 35; (1984); p. 3897 - 3900 View in Reaxys

F HO F I

CO2 HO

Rx-ID: 5728229 View in Reaxys 668/1037 Yield

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N F

HO F

N O

CO2 HO

Rx-ID: 6211699 View in Reaxys 669/1037 Yield

Conditions & References With dibenzoyl peroxide, iron(III) in acetonitrile, T= 80 °C , Yield given. Yields of byproduct given Castaldi, Graziano; Minisci, Francesko; Tortelli, Vito; Vismara, Elena; Tetrahedron Letters; vol. 25; nb. 35; (1984); p. 3897 - 3900 View in Reaxys O F

I F

1.)Nafion H

F F F

Rx-ID: 6585462 View in Reaxys 670/1037 Yield

Conditions & References With 1-thiopropane, 1.)in trifluoroacetic acid-trifluoroacetic anhidrid, 0 deg C, 6 h, then at room temp., 4 d,, Yield given. Multistep reaction Umemoto, Teruo; Tetrahedron Letters; vol. 25; nb. 1; (1984); p. 81 - 82 View in Reaxys

chloroiodobenzenes

Rx-ID: 6727077 View in Reaxys 671/1037 Yield

Conditions & References With iodine, T= 275 °C , Product distribution Mulder, Peter; Louw, Robert; Recueil: Journal of the Royal Netherlands Chemical Society; vol. 103; nb. 10; (1984); p. 282 287 View in Reaxys

N F HO F I

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CO2 HO

Rx-ID: 6727258 View in Reaxys 672/1037 Yield

F HO

F I

CO2 HO

Rx-ID: 7072232 View in Reaxys 673/1037 Yield

I+ Cl –

O H

HCl

N O

Rx-ID: 7454313 View in Reaxys 674/1037 Yield

Conditions & References Irradiation, with a 2-methoxy-2H-pyrane as proptnic acid indicator, Quantum yield Weissenfels, Manfred; Putz, Dietmar; Timpe, Hans-Joachim; Baumann, Harald; Fischer, Gerhard W.; Zimmermann, Thomas; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 24; nb. 8; (1984); p. 287 - 288 View in Reaxys

235/330

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I+

N Cl –

HCl

Rx-ID: 8276542 View in Reaxys 675/1037 Yield

Conditions & References With 9,10-phenanthrenquinoline, Irradiation, with a 2-methoxy-2H-pyrane as protonic acid indicator, Quantum yield Weissenfels, Manfred; Putz, Dietmar; Timpe, Hans-Joachim; Baumann, Harald; Fischer, Gerhard W.; Zimmermann, Thomas; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 24; nb. 8; (1984); p. 287 - 288 View in Reaxys

N F

HO F

CO2 HO

Rx-ID: 8426384 View in Reaxys 676/1037 Yield

N I

HO F

O N

CO2 HO

Rx-ID: 8426385 View in Reaxys 677/1037 Yield

N I

F HO F

236/330

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CO2 HO

Rx-ID: 8426386 View in Reaxys 678/1037 Yield

F HO F

CO2 HO

Rx-ID: 8426387 View in Reaxys 679/1037 Yield

HO F I

CO2 HO

Rx-ID: 8426388 View in Reaxys 680/1037 Yield

237/330

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I+

O Cl –

Rx-ID: 1584185 View in Reaxys 681/1037 Yield 26 % Chromat., 32 % Chromat., 37 % Chromat., 5 % Chromat.

Conditions & References With zinc, palladium diacetate, Time= 1h, Ambient temperature, different diaryliodonium salts, metals, pressures of carbon monoxide and solvents, Product distribution Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1201 - 1202 View in Reaxys

I+

Br–

Rx-ID: 1585275 View in Reaxys 682/1037 Yield 33 % Chromat., 62 % Chromat.

Conditions & References With Copper(I); benzoate, Time= 2.08333h, T= 23 °C , various reaction conditions, Product distribution, Mechanism Lockhart, Thomas P.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1940 - 1946 View in Reaxys -1 F

F AsF F F (v6) F

I+

Rx-ID: 1596635 View in Reaxys 683/1037 Yield

Conditions & References

6 % ChroWith copper(II) benzoate, Time= 2h, T= 120 °C , various solvents and catalyst concentrations under different reaction condimat., 82 % tions, Product distribution, Mechanism Chromat., 1 % Chromat. Lockhart, Thomas P.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1940 - 1946 View in Reaxys -1 F (v4)

B FF

I I

N+ N

Rx-ID: 1744882 View in Reaxys 684/1037 Yield

Conditions & References With pyrene in acetonitrile, Irradiation, CIDNP effects of the photochemical dediazonation; reaction in the absence of pyrene in dioxane Becker, Heinz G. O.; Pfeifer, Dietmar; Radeglia, Reiner; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 38; nb. 12; (1983); p. 1591 - 1597 View in Reaxys

238/330

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I N

Rx-ID: 1975013 View in Reaxys 685/1037 Yield

Conditions & References With sulfonic acid resin (H+ form, Bio-Rad AG 50W-12), sodium iodide in acetonitrile, Time= 0.133333h, T= 75 °C Satyamurthy, Nagichettiar; Barrio, Jorge R.; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4394 - 4396 View in Reaxys With sulfonic acid resin (H+ form, Bio-Rad AG 50W-X12), sodium iodide in acetonitrile, Time= 0.133333h, T= 75 °C , other reagents: CF3COOH, CH3SO3H; var. 1-aryl-3,3-diethyltriazenes, Product distribution Satyamurthy, Nagichettiar; Barrio, Jorge R.; Journal of Organic Chemistry; vol. 48; nb. 23; (1983); p. 4394 - 4396 View in Reaxys

O O O

Rx-ID: 1994917 View in Reaxys 686/1037 Yield

Conditions & References

80 %

in chloroform Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys

F O

Rx-ID: 2005609 View in Reaxys 687/1037 Yield

Conditions & References

82 %

With ethyl iodide, bis-[(trifluoroacetoxy)iodo]benzene in chloroform, Time= 2h Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys

I+ C

Cl –

Rx-ID: 2241003 View in Reaxys 688/1037 Yield 60 % Chromat., 18 % Chromat.,

Conditions & References With zinc, palladium diacetate in acetone, Time= 1h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1201 - 1202

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21 % Chromat.

View in Reaxys

I+ Cl –

Rx-ID: 2241022 View in Reaxys 689/1037 Yield

Conditions & References

80 %

With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.0333333h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys

I+ C

Br–

Rx-ID: 2254933 View in Reaxys 690/1037 Yield

Conditions & References

61 % Chromat., 23 % Chromat., 16 % Chromat.

With zinc, palladium diacetate in acetone, Time= 1h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1201 - 1202 View in Reaxys

I+ Br–

I Cl

Rx-ID: 2326944 View in Reaxys 691/1037 Yield 90 %

Conditions & References With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.05h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys H 2N

O O N

I NH

Rx-ID: 2407649 View in Reaxys 692/1037 Yield 79 %, 12 %

Conditions & References With copper, Time= 12h, T= 210 °C

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Yamamoto, Takakazu; Kurata, Yasundo; Canadian Journal of Chemistry; vol. 61; (1983); p. 86 - 91 View in Reaxys

I+ I–

Rx-ID: 2428810 View in Reaxys 693/1037 Yield

Conditions & References

50 % Chromat.

With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.166667h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys

I+ Br–

Rx-ID: 2429216 View in Reaxys 694/1037 Yield

Conditions & References

91 %

With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.05h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys

I+ Br–

Rx-ID: 2429218 View in Reaxys 695/1037 Yield

Conditions & References

91 %

With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.05h, Ambient temperature, different catalysts, diaryliodonium salts and reaction times or without catalyst, Product distribution Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys

I+ Br–

Rx-ID: 2429542 View in Reaxys 696/1037 Yield

Conditions & References

91 %

I+

Br– O

Rx-ID: 2429671 View in Reaxys 697/1037 Yield 82 %

Conditions & References With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.166667h, Ambient temperature

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Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys

I+

Br–

Rx-ID: 2429680 View in Reaxys 698/1037 Yield

Conditions & References

93 %

With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.0666667h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys

I+ Br–

O O

N N

N O

Rx-ID: 2429981 View in Reaxys 699/1037 Yield

Conditions & References

91 %

With zinc, palladium(II) acetylacetonate in tetrahydrofuran, Time= 0.5h, Ambient temperature Uchiyama, Masaharu; Suzuki, Takehiko; Yamazaki, Yasuo; Chemistry Letters; (1983); p. 1165 - 1166 View in Reaxys F F F F

O I

I O

Rx-ID: 2855087 View in Reaxys 700/1037 Yield

Conditions & References With para-xylene in chloroform, Time= 2h Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys -1

I+ F F

F (v6)P

(v1)

Rx-ID: 3187712 View in Reaxys 701/1037 Yield

Conditions & References in methanol, Irradiation, other solvents: acetonitrile, isobutylglycidether, Mechanism, Kinetics

242/330

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Klemm, Elisabeth; Riesenberg, Evelin; Graness, Angelika; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 23; nb. 6; (1983); p. 222 View in Reaxys

I N

S O

H 2N

Rx-ID: 3266706 View in Reaxys 702/1037 Yield

Conditions & References With sodium hydrogensulfite Breslow, Ronald; Gellman, Samuel H.; Journal of the American Chemical Society; vol. 105; nb. 22; (1983); p. 6728 - 6729 View in Reaxys F F F O O

I O

F F

Rx-ID: 3385543 View in Reaxys 703/1037 Yield

Conditions & References

18 %

With tetramethlyammonium chloride in chloroform Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys

I HO

Rx-ID: 3552590 View in Reaxys 704/1037 Yield

Conditions & References With iodine, mercury(II) oxide in nitrobenzene, Time= 2h, T= 180 - 185 °C Uemura, Sakae; Tanaka, Sakuya; Okano, Masaya; Hamana, Masatomo; Journal of Organic Chemistry; vol. 48; nb. 19; (1983); p. 3297 - 3301 View in Reaxys -1

(v4)

B FF

N+ N

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I O

O O

Rx-ID: 3792948 View in Reaxys 705/1037 Yield

Conditions & References

41 % Chromat., 45 % Chromat.

With copper in dimethyl sulfoxide, Time= 1h, T= 20 °C , different quinone/isopropyl iodide ratio; other catalyst, other time, Rate constant, Mechanism, Product distribution Citterio, Attilio; Vismara, Elena; Bernardi, Rosanna; Journal of Chemical Research, Miniprint; nb. 4; (1983); p. 876 - 890 View in Reaxys

HO O

O H

Rx-ID: 3827382 View in Reaxys 706/1037 Yield

Conditions & References in acetic acid, T= 24.9 °C , other temperatures; ΔH(excit.), ΔG(excit.), ΔS(excit.), ΔH, ΔG, ΔS, Rate constant, Thermodynamic data, Equilibrium constant Saiprakash, P. K.; Rajanna, K. Chinna; Devi, Y. Uma; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 3; (1983); p. 292 - 294 View in Reaxys in water, acetic acid, T= 31.9 °C , velocity constants, further temp., var. conc. of educts, activation energy, formation konstant K, ΔH(excit.), ΔG(excit.), ΔS(excit.), ΔH, ΔS, ΔG, effect of variation of solvent (var. percentage of HOAc in water, 318 K), Thermodynamic data, Kinetics, Mechanism Chinna Rajanna, K.; Venkateshwer Rao, G.; Saiprakash, P. K.; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 263; nb. 5; (1982); p. 1025 - 1033 View in Reaxys

N O

O O

O S

S Cl

Rx-ID: 3879974 View in Reaxys 707/1037

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Yield

Conditions & References

78 %, 1 %

in tetrachloromethane, Time= 2h, T= 0 °C , Product distribution Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys

O O

I O

Rx-ID: 3918636 View in Reaxys 708/1037 Yield

Conditions & References in benzene, Time= 17h, Heating, Yield given Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys

O O

HO O

Rx-ID: 3918638 View in Reaxys 709/1037 Yield

Conditions & References With iodine in benzene, Time= 33h, T= 79 °C , Yield given Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys With iodine in benzene, Time= 13h, Heating, Yield given Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys F F F O

O O

I O

F F

iodine

Rx-ID: 7078927 View in Reaxys 710/1037

245/330

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Yield 100 % Spectr.

Conditions & References in chloroform Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys F F F O O O

F F

F Cl

iodine

Rx-ID: 7078928 View in Reaxys 711/1037 Yield 20 %, 68 %

O O

I O

F F

O F

iodine

F F

Rx-ID: 7078931 View in Reaxys 712/1037 Yield 32 %

Conditions & References in chloroform, Ambient temperature, Further byproducts given Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys

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O O I O

iodine

O O

Rx-ID: 7454801 View in Reaxys 713/1037 Yield 85 %

Conditions & References in chloroform, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys F F F O O O

I O

F F

O F F

iodine

Rx-ID: 7454802 View in Reaxys 714/1037 Yield 54 %

F O F Cl

Cl F

iodine

Rx-ID: 7454803 View in Reaxys 715/1037

247/330

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Yield 21 %

Conditions & References in chloroform, Further byproducts given Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys

O I O

iodine

Rx-ID: 7454804 View in Reaxys 716/1037 Yield 70 %

I O

F F

I F

iodine

Rx-ID: 7454805 View in Reaxys 717/1037 Yield 79 %

248/330

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F F F O O

I O

F F

iodine

Rx-ID: 7454806 View in Reaxys 718/1037 Yield 48 %

I O

F F

O F

F F

iodine Rx-ID: 7454809 View in Reaxys 719/1037 Yield 43 %

I O

249/330

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F F

O F

iodine

O F

Rx-ID: 7454810 View in Reaxys 720/1037 Yield 55 %

O I O I

O O

iodine

Rx-ID: 7923466 View in Reaxys 721/1037 Yield 74 %

I O

F O O

I O F

F F

iodine

Rx-ID: 7923467 View in Reaxys 722/1037 Yield 8 %, 26 %

Conditions & References in chloroform

250/330

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Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys F F F I

O O O

F F

F F F

I HO

iodine

Rx-ID: 8450329 View in Reaxys 723/1037 Yield 26 %

Conditions & References in chloroform, Time= 480h Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys in chloroform, Time= 480h Gallos, John; Varvoglis, Anastasios; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 1999 - 2002 View in Reaxys O O I

O O

I O

Rx-ID: 1579414 View in Reaxys 724/1037 Yield 88 %

Conditions & References With sodium methylate, Time= 48h, T= 0 - 25 °C , Var. aldazines and alcohols, Product distribution Moriarty, Robert M.; Hu, Henry; Tetrahedron Letters; vol. 23; nb. 15; (1982); p. 1537 - 1540 View in Reaxys

I Br

Rx-ID: 1769121 View in Reaxys 725/1037

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Yield

Conditions & References

80 %

With bromine, bis-[(trifluoroacetoxy)iodo]benzene in chloroform, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys O

Rx-ID: 1834299 View in Reaxys 726/1037 Yield

Conditions & References

73 %

With bromine, bis-[(trifluoroacetoxy)iodo]benzene in chloroform, Time= 3h, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys O

Rx-ID: 1834300 View in Reaxys 727/1037 Yield

Conditions & References

93 %

With aluminium trichloride, bis-[(trifluoroacetoxy)iodo]benzene in chloroform, Time= 2h, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

O O Cl

O I

Rx-ID: 1995035 View in Reaxys 728/1037 Yield 48 %, 41 %

Conditions & References With aluminium trichloride in cyclohexane, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys O

O N

I N O

O O

Rx-ID: 2005468 View in Reaxys 729/1037 Yield 25 %

Conditions & References Semenov, V. V.; Bruskin, A. B.; Shevelev, S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 12; (1982); p. 2423 - 2427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1982); p. 2741 - 2746 View in Reaxys

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I Cl

Rx-ID: 2008558 View in Reaxys 730/1037 Yield 38 %

Conditions & References With aluminium trichloride, bis-[(trifluoroacetoxy)iodo]benzene in chloroform, Time= 1h, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

Cl Cl

Rx-ID: 2061621 View in Reaxys 731/1037 Yield 45 %, 40 %

Conditions & References With aluminium trichloride in chloroform, Time= 1h, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

45 %, 40 %

With aluminium trichloride in chloroform, Time= 1h, Ambient temperature, further solvent, Product distribution Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

38 %, 29 %

With aluminium trichloride in cyclohexane, Time= 12h, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

I+

–O

Na +

O N O

O O

O N

Rx-ID: 2281806 View in Reaxys 732/1037 Yield

Conditions & References in water, T= 60 °C , relative rates of decomposition of the 9-I-2 intermediate, Product distribution, Mechanism Tanner, Dennis D.; Reed, Darwin W.; Setiloane, B.P.; Journal of the American Chemical Society; vol. 104; nb. 14; (1982); p. 3917 - 3923 View in Reaxys

I+ –O

Na +

Cl –

253/330

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I I

Rx-ID: 2281807 View in Reaxys 733/1037 Yield

I+ –O

Br I–

Na +

I I

Rx-ID: 2281808 View in Reaxys 734/1037 Yield

I+ O –O

I–

Na +

I O

Rx-ID: 2281809 View in Reaxys 735/1037 Yield

I+ –O

Na +

Br–

Rx-ID: 2281810 View in Reaxys 736/1037 Yield

Conditions & References in water, T= 60 °C , relative rates of decomposition of the 9-I-2 intermediate, Product distribution, Mechanism

254/330

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Tanner, Dennis D.; Reed, Darwin W.; Setiloane, B.P.; Journal of the American Chemical Society; vol. 104; nb. 14; (1982); p. 3917 - 3923 View in Reaxys

I+ –O

O Cl –

Na +

Rx-ID: 2281811 View in Reaxys 737/1037 Yield

I+ –O

Br–

Na +

Rx-ID: 2281812 View in Reaxys 738/1037 Yield

–O

O N

Br–

Na +

O I

N O

O O

Rx-ID: 2281814 View in Reaxys 739/1037 Yield

255/330

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I+ –

Na +

Rx-ID: 2281880 View in Reaxys 740/1037 Yield

–O

I–

Na +

I N

Rx-ID: 2281886 View in Reaxys 741/1037 Yield

I+ –O

O I–

Na +

Rx-ID: 2281887 View in Reaxys 742/1037 Yield

–O

Na +

I+ F

I–

256/330

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F F

Rx-ID: 2281888 View in Reaxys 743/1037 Yield

I+

O Li+

Br–

O–

Rx-ID: 2326324 View in Reaxys 744/1037 Yield

Conditions & References

37 %, 6 %, 54 %

in methanol, Time= 48h, T= 30 °C , Further byproducts given Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+

O Li+

N O

Br–

–

Rx-ID: 2326325 View in Reaxys 745/1037 Yield

Conditions & References

37 %, 2 %, 54 %

in methanol, Time= 48h, T= 30 °C , Further byproducts given Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+

O Li+

Br–

O–

I O

N O

Rx-ID: 2326326 View in Reaxys 746/1037 Yield

Conditions & References

37 %, 54 %, in methanol, Time= 48h, T= 30 °C , Further byproducts given 24 % Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358

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View in Reaxys

I+

O Li+

Br–

O–

I N

Rx-ID: 2326327 View in Reaxys 747/1037 Yield

Conditions & References

37 %, 54 %, in methanol, Time= 48h, T= 30 °C , Further byproducts given 16 % Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+

O Li+

Br–

O–

Rx-ID: 2326328 View in Reaxys 748/1037 Yield

Conditions & References

35 %, 57 %, in methanol, Time= 48h, T= 30 °C , Further byproducts given 3% Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+ F O F O O–

F F

Rx-ID: 2331323 View in Reaxys 749/1037 Yield

Conditions & References

57.4 %, With potassium fluoride, Time= 4h, T= 165 - 170 °C , Further byproducts given 56.8 %, 9 % Puy, Michael van der; Journal of Fluorine Chemistry; vol. 21; (1982); p. 385 - 392 View in Reaxys

I+

O N

Li+

Br–

O–

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O O

N O

Rx-ID: 2429210 View in Reaxys 750/1037 Yield

Conditions & References

38 %, 5 %, 5 %, 41 %, 43 %

in methanol, Time= 48h, T= 30 °C , other diaryliodonium bromides, other times, effect of light and oxygen, Mechanism, Product distribution Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+

O Li+

Br–

O–

I N

Rx-ID: 2429211 View in Reaxys 751/1037 Yield

Conditions & References

38 %, 41 %, in methanol, Time= 48h, T= 30 °C , Further byproducts given 43 % Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+

O Li+

N O

Br–

–

O N

O O

Rx-ID: 2429212 View in Reaxys 752/1037 Yield

Conditions & References

2 %, 67 %, 8%

With isopropenylbenzene in methanol, Time= 48h, T= 30 °C , Further byproducts given Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

I+

O Li+

N O–

Br– O

N O

Rx-ID: 2429604 View in Reaxys 753/1037 Yield

Conditions & References

35 %, 57 %, in methanol, Time= 48h, T= 30 °C , Further byproducts given 28 % Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358

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View in Reaxys

I+

O Li+

Br–

O–

Rx-ID: 2429605 View in Reaxys 754/1037 Yield

Conditions & References

35 %, 57 %, in methanol, Time= 48h, T= 30 °C , Further byproducts given 13 % Singh, P. R.; Khanna, R. K.; Tetrahedron Letters; vol. 23; nb. 50; (1982); p. 5355 - 5358 View in Reaxys

Cl –

Rx-ID: 3149512 View in Reaxys 755/1037 Yield

Conditions & References in gas, T= 26 °C , p= 0 - 0.3Torr , Equilibrium constant French, M. A.; Ikuta, S.; Kebarle, P.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1907 - 1918 View in Reaxys F F F Cl

O O

I O

I I

Rx-ID: 3779243 View in Reaxys 756/1037 Yield 46 %, 35 %

Conditions & References With chlorine in chloroform, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

44 %, 38 %

With aluminium trichloride in cyclohexane, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

34 %, 29 %

With (Dichloroiodo)benzene in chloroform, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

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O N

I N O

O O

Rx-ID: 3861000 View in Reaxys 757/1037 Yield

Conditions & References

10 %

T= 20 °C Semenov, V. V.; Bruskin, A. B.; Shevelev, S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 12; (1982); p. 2423 - 2427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1982); p. 2741 - 2746 View in Reaxys Cl

I Cl

Rx-ID: 3861130 View in Reaxys 758/1037 Yield

Conditions & References

63 %

With aluminium trichloride, bis-[(trifluoroacetoxy)iodo]benzene in chloroform, Time= 1h, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys O

O N

I N O

Rx-ID: 3917501 View in Reaxys 759/1037 Yield 71 %

Conditions & References With copper acetylacetonate in benzene, Time= 1h, T= 6 °C , influence of temperature and reagents on the decomposition time of phenyliodonium dinitromethylide, Product distribution Semenov, V. V.; Bruskin, A. B.; Shevelev, S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 12; (1982); p. 2423 - 2427; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1982); p. 2741 - 2746 View in Reaxys

Rx-ID: 3918727 View in Reaxys 760/1037 Yield 80 %

Conditions & References With aluminium trichloride, bis-[(trifluoroacetoxy)iodo]benzene, Ambient temperature Gallos, John; Varvoglis, Anastasios; Journal of Chemical Research, Miniprint; nb. 6; (1982); p. 1649 - 1660 View in Reaxys

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S Sn

Rx-ID: 26843209 View in Reaxys 761/1037 Yield

Conditions & References With iodine in tetrachloromethane, Kinetics, to soln. of Sn compd. I2 added dropwise, soln. left until became colourless Wardell, James L.; Wigzell, John McM.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1982); p. 2321 - 2326 ; (from Gmelin) View in Reaxys

Rx-ID: 26949553 View in Reaxys 762/1037 Yield

Conditions & References With iodine in tetrachloromethane, Kinetics, to soln. of Sn compd. I2 added dropwise, soln. left until become colourless Wardell, James L.; Wigzell, John McM.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1982); p. 2321 - 2326 ; (from Gmelin) View in Reaxys

I Sn

Rx-ID: 26950440 View in Reaxys 763/1037 Yield

N N N

I O

N N

Rx-ID: 1840225 View in Reaxys 764/1037 Yield 74 %

Conditions & References in dichloromethane, Ambient temperature Moriarty, Robert M.; Gupta, Satish C.; Hu, Henry; Berenschot, Daniel M.; White, Kenneth B.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 686 - 688 View in Reaxys

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I B

Rx-ID: 2044587 View in Reaxys 765/1037 Yield

Conditions & References With sodium methylate, Iodine monochloride, 1) THF, methanol; 2) methanol, THF, Yield given. Multistep reaction Kabalka, George W.; Gooch, E. Eugene; Hsu, Henry C.; Synthetic Communications; vol. 11; nb. 3; (1981); p. 247 - 252 View in Reaxys

F S F

F F

Rx-ID: 2213559 View in Reaxys 766/1037 Yield 57 % Chromat.

Conditions & References in pentane, Time= 1h, T= 0 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys F

O S

O O

F F

I F

Rx-ID: 2213561 View in Reaxys 767/1037 Yield 70 % Chromat.

Conditions & References in tetrahydrofuran, Time= 1h, T= -78 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys

I+ Cl –

(v1)

–Cl

(v2)

Hg +

Rx-ID: 2241026 View in Reaxys 768/1037 Yield

Conditions & References With mercury in acetonitrile, Time= 22h, T= 45 °C , other temperatures, Ea, ΔS298 K, Kinetics, Thermodynamic data

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Kim, T. L.; Ptitsyna, O. A.; Butin, K. P.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 12; (1981); p. 2244 - 2247; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1981); p. 2699 - 2703 View in Reaxys F

F S F Cl

O F

F F

Rx-ID: 2292005 View in Reaxys 769/1037 Yield

Conditions & References

58 % Chromat.

in tetrahydrofuran, diethyl ether, Time= 1h, T= -78 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys

I+ Br–

Rx-ID: 2429217 View in Reaxys 770/1037 Yield

Conditions & References With mercury in acetonitrile, Time= 22h, T= 45 °C , other temperatures, Ea, ΔS298 K, Kinetics, Thermodynamic data Kim, T. L.; Ptitsyna, O. A.; Butin, K. P.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 12; (1981); p. 2244 - 2247; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1981); p. 2699 - 2703 View in Reaxys

NH O

F F

O–

I +I

Rx-ID: 2439782 View in Reaxys 771/1037 Yield

Conditions & References

75 %

With lithium bromide in N,N-dimethyl-formamide, Time= 2h, T= 100 °C Budylin, V. A.; Ermolenko, M. S.; Chugtai, F. A.; Kost, A. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 11; (1981); p. 1088 - 1090; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 11; (1981); p. 1494 1496 View in Reaxys

NH O

NH F

O–

I Cl

Rx-ID: 2439784 View in Reaxys 772/1037

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Yield

Conditions & References

25 %, 64 %

With tetrabutyl-ammonium chloride in N,N-dimethyl-formamide, Time= 2h, T= 100 °C Budylin, V. A.; Ermolenko, M. S.; Chugtai, F. A.; Kost, A. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 11; (1981); p. 1088 - 1090; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 11; (1981); p. 1494 1496 View in Reaxys

NH NH

O–

I +I

Rx-ID: 2439785 View in Reaxys 773/1037 Yield 80 %

Conditions & References With lithium chloride in N,N-dimethyl-formamide, Time= 2h, T= 100 °C Budylin, V. A.; Ermolenko, M. S.; Chugtai, F. A.; Kost, A. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 11; (1981); p. 1088 - 1090; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 11; (1981); p. 1494 1496 View in Reaxys

F I

F O

O F

F F F

F F

Rx-ID: 2440876 View in Reaxys 774/1037 Yield 47 %

Conditions & References in tetrahydrofuran, diethyl ether, Time= 1h, T= -78 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys F

F S F

Mg Cl

O F

F F

Rx-ID: 2442018 View in Reaxys 775/1037 Yield 60 % Chromat.

Conditions & References in tetrahydrofuran, diethyl ether, Time= 1h, T= -110 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200

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View in Reaxys

I Si

Si Cl

Rx-ID: 2835370 View in Reaxys 776/1037 Yield

Conditions & References

74 %

With Iodine monochloride, Time= 20h, T= 70 °C Wiberg, Nils; Preiner, Gerhard; Schieda, Oswald; Chemische Berichte; vol. 114; nb. 6; (1981); p. 2087 - 2103 View in Reaxys

I Si

Si I

Rx-ID: 2835371 View in Reaxys 777/1037 Yield 60 %

Conditions & References With iodine, Time= 8h, T= 130 °C Wiberg, Nils; Preiner, Gerhard; Schieda, Oswald; Chemische Berichte; vol. 114; nb. 6; (1981); p. 2087 - 2103 View in Reaxys O

I O

Rx-ID: 3382778 View in Reaxys 778/1037 Yield 60 %

Conditions & References With sodium hydroxide in methanol, T= 10 °C , var. arylmethylketones, Product distribution Moriarty, Robert M.; Hu, Henry; Gupta, Satish C.; Tetrahedron Letters; vol. 22; nb. 14; (1981); p. 1283 - 1286 View in Reaxys F F

F F

O O

I O

F F

Rx-ID: 3779178 View in Reaxys 779/1037 Yield 54 %

Conditions & References With trifluoroacetic acid in chloroform, Time= 1h, T= -10 °C

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Shabarov, Yu. S.; Pisanova, E. V.; Saginova, L. G.; Journal of Organic Chemistry USSR (English Translation); vol. 17; (1981); p. 1685 - 1689; Zhurnal Organicheskoi Khimii; vol. 17; nb. 9; (1981); p. 1886 - 1892 View in Reaxys F F F

F O

Rx-ID: 3841543 View in Reaxys 780/1037 Yield

Conditions & References

82 % Chromat.

in tetrahydrofuran, diethyl ether, Time= 2h, T= -110 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys

F I

F F

Mg Cl

O F

F F

Rx-ID: 3841547 View in Reaxys 781/1037 Yield

Conditions & References

36 % Chromat.

in tetrahydrofuran, diethyl ether, 0.5 h at -78 deg C then 0.5 h from -78 deg C to -45 deg C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys

F S F

O F

I F

F F

Rx-ID: 3862624 View in Reaxys 782/1037 Yield 57 % Chromat.

Conditions & References in tetrahydrofuran, Time= 1h, T= -110 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys

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F F

F S

F F

Rx-ID: 3862626 View in Reaxys 783/1037 Yield

Conditions & References

44 % Chromat.

in tetrahydrofuran, Time= 1h, T= -110 °C Umemoto, Teruo; Kuriu, Yuriko; Tetrahedron Letters; vol. 22; nb. 51; (1981); p. 5197 - 5200 View in Reaxys O

polyester, 63percent

Rx-ID: 6218714 View in Reaxys 784/1037 Yield

Conditions & References in dichloromethane, Ambient temperature, other ratio of educts; other ketenes; δ-lactone intermediate, Mechanism, Product distribution Moriarty, Robert M.; Gupta, Satish C.; Hu, Henry; Berenschot, Daniel M.; White, Kenneth B.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 686 - 688 View in Reaxys

I O

polyester, 90percent

Rx-ID: 6218715 View in Reaxys 785/1037 Yield

polyester, 67percent

Rx-ID: 7084985 View in Reaxys 786/1037 Yield

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polyester, 81percent

Rx-ID: 7084986 View in Reaxys 787/1037 Yield

O N O

CO2

HO O

O N O

Rx-ID: 7452244 View in Reaxys 788/1037 Yield

Conditions & References

30 %

in 1,4-dioxane, Ambient temperature, other δ-ketoacids; cyclic intermediate, Mechanism, Product distribution Moriarty, Robert M.; Gupta, Satish C.; Hu, Henry; Berenschot, Daniel M.; White, Kenneth B.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 686 - 688 View in Reaxys F

F F

polyester, 32percent

F O

Rx-ID: 7457273 View in Reaxys 789/1037 Yield

Conditions & References in dichloromethane, Ambient temperature, other ratio of educts; other ketenes; δ-lactone intermediate (isolated for tetracyanoethylene as oxygen acceptor), Mechanism, Product distribution Moriarty, Robert M.; Gupta, Satish C.; Hu, Henry; Berenschot, Daniel M.; White, Kenneth B.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 686 - 688 View in Reaxys

H 2N

ethane-δ.δ-bis-sulfonic acid chloride

HNO3+H2SO4 Rx-ID: 19165130 View in Reaxys 790/1037

Yield

Conditions & References Reaction Steps: 2 1: 1) conc. HCl, NaNO2, 2) K2CO3 / 1) H2O, 0 deg C, 30 min, 2) ice-water 2: 65 percent / Me3SiCl, NaI / acetonitrile / 0.08 h / 60 °C With hydrogenchloride, chloro-trimethyl-silane, potassium carbonate, sodium iodide, sodium nitrite in acetonitrile Ku, Hao; Barrio, Jorge R.; Journal of Organic Chemistry; vol. 46; (1981); p. 5239 - 5241 View in Reaxys

I+ Br–

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Br2Hg 2

(v2)

Rx-ID: 26081872 View in Reaxys 791/1037 Yield

Conditions & References

6-7, 1.4 %

in acetonitrile, Kinetics, byproducts: C6H5Br; at different temp. between 20-70°C; UV; yields for 45°C Kim, T. L.; Ptitsyna, O. A.; Butin, K. P.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 12; (1981); p. 2244 - 2247; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1981); p. 2699 - 2703 ; (from Gmelin) View in Reaxys

I+ Cl –

Cl 2Hg 2

(v1)

–Cl

(v2)

Hg +

Rx-ID: 26138560 View in Reaxys 792/1037 Yield

Conditions & References

10-11, 4-5, 89-92, 1.4 %

in acetonitrile, Kinetics, at different temp. between 20-70°C; UV; yields for 45°C Kim, T. L.; Ptitsyna, O. A.; Butin, K. P.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 12; (1981); p. 2244 - 2247; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1981); p. 2699 - 2703 ; (from Gmelin) View in Reaxys

-1 F (v4)

B FF

I+

I F

Cu +

B– FF

Rx-ID: 26431713 View in Reaxys 793/1037 Yield <1, 95 %, 99 %, 5 %

Conditions & References in acetonitrile, Kinetics, stirred at 20-70°C; GLC Ptitsyna, O. A.; Kim, T. L.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 10; (1981); p. 1966 - 1967; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1981); p. 2386 - 2388 ; (from Gmelin) View in Reaxys

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O S

I S N O

Rx-ID: 1457133 View in Reaxys 794/1037 Yield

Conditions & References

82 % Spectr.

With copper acetylacetonate in acetonitrile, 1.) -20 deg C, 5 min, 2.) 40 min Semenov, V. V.; Mel'nikova, L. G.; Shevelev S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 29; nb. 1; (1980); p. 123 - 129; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1980); p. 138 - 144 View in Reaxys

Rx-ID: 1711212 View in Reaxys 795/1037 Yield

Conditions & References

15 % Chromat.

With tributylphosphine, potassium iodide, nickel dibromide in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 1.5h, T= 50 °C , other aryl bromides, var. catalysts, var. solvents, var. temp., var. time, Product distribution Takagi, Kentaro; Hayama, Naomi; Inokawa, Saburo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 12; (1980); p. 3691 - 3695 View in Reaxys

15 % Chromat.

With tributylphosphine, potassium iodide, nickel dibromide in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 1.5h, T= 50 °C Takagi, Kentaro; Hayama, Naomi; Inokawa, Saburo; Bulletin of the Chemical Society of Japan; vol. 53; nb. 12; (1980); p. 3691 - 3695 View in Reaxys

O N

I Se

Rx-ID: 1742371 View in Reaxys 796/1037 Yield 80 %

Conditions & References in diethyl ether, acetic anhydride, Time= 0.333333h, T= 20 °C Semenov, V. V.; Mel'nikova, L. G.; Shevelev S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 29; nb. 1; (1980); p. 123 - 129; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1980); p. 138 - 144 View in Reaxys O

O N

N O

O O

Rx-ID: 1912838 View in Reaxys 797/1037 Yield 30 % Spectr.

Conditions & References With copper acetylacetonate in acetonitrile, 1.) -20 deg C, 20 min, 2.) 40 min

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Semenov, V. V.; Mel'nikova, L. G.; Shevelev S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 29; nb. 1; (1980); p. 123 - 129; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1980); p. 138 - 144 View in Reaxys O

O N

N N

O N

O S+

N S

O–

Rx-ID: 1939111 View in Reaxys 798/1037 Yield

Conditions & References

85 %

in acetonitrile, Time= 0.333333h, T= -20 °C Semenov, V. V.; Mel'nikova, L. G.; Shevelev S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 29; nb. 1; (1980); p. 123 - 129; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1980); p. 138 - 144 View in Reaxys

O O O

I–

(v2) I–

N+

N+ O

Rx-ID: 1994975 View in Reaxys 799/1037 Yield

Conditions & References

92 %

in chloroform, Time= 2h, Ambient temperature Doleschall, Gabor; Toth, Gabor; Tetrahedron; vol. 36; (1980); p. 1649 - 1666 View in Reaxys

N+ N

O O

I I–

N+

I–

N S

Rx-ID: 1994980 View in Reaxys 800/1037 Yield 31 %

Conditions & References With sulfuric acid, iodine, sodium methylate, potassium iodide, 1.) CHCl3, 2.) MeOH, room temp, 15 min, Yield given. Multistep reaction

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Doleschall, Gabor; Toth, Gabor; Tetrahedron; vol. 36; (1980); p. 1649 - 1666 View in Reaxys

O N

I Se+

N O

O–

O N

Rx-ID: 2072623 View in Reaxys 801/1037 Yield

Conditions & References

in acetonitrile, Time= 0.5h, T= -20 °C Semenov, V. V.; Mel'nikova, L. G.; Shevelev S. A.; Fainzil'berg, A. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 29; nb. 1; (1980); p. 123 - 129; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1980); p. 138 - 144 View in Reaxys -1 F (v4)

F O–

B FF

Na +

Rx-ID: 2273312 View in Reaxys 802/1037 Yield

Conditions & References

55.0 % Chromat., 1.2 % Chromat., 21.9 % Chromat., 14.6 % Chromat., 26.9 % Chromat.

in ethanol, Time= 3h, T= 71 °C , Product distribution, Mechanism Lubinkowski, Jacek J.; Arrieche, Cecilia Gimenez; McEwen, William E.; Journal of Organic Chemistry; vol. 45; nb. 11; (1980); p. 2076 - 2079 View in Reaxys

-1 F (v4)

F O–

B FF

Na +

I+

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Rx-ID: 2273462 View in Reaxys 803/1037 Yield 44.9 % Chromat., 10.5 % Chromat., 24.2 % Chromat., 14.6 % Chromat., 20.3 % Chromat.

Conditions & References in ethanol, Time= 3h, T= 71 °C , Product distribution, Mechanism Lubinkowski, Jacek J.; Arrieche, Cecilia Gimenez; McEwen, William E.; Journal of Organic Chemistry; vol. 45; nb. 11; (1980); p. 2076 - 2079 View in Reaxys

H 2N

CS2

Rx-ID: 21271353 View in Reaxys 804/1037 Yield

Conditions & References Reaction Steps: 2 1: 1.) conc.HCl, NaNO2(aq) 2.) KOH(aq) / 1.) ice bath, 5 min. 2.) 5 deg C, 10 min. 2: KI, HCl / H2O With hydrogenchloride, potassium hydroxide, potassium iodide, sodium nitrite in water Foster, Natalie I.; Heindel, Ned D.; Burns, Donald H.; Muhr, William; Synthesis; nb. 7; (1980); p. 572 - 573 View in Reaxys F

O I

Rx-ID: 25332514 View in Reaxys 805/1037 Yield

Conditions & References 18.25 : EXAMPLES 18-25 EXAMPLES 18-25 A mixture of o-fluoroiodobenzene (44.4g, 0.2 mole), 4-isopropylphenol (27.2g, 0.2 mole), copper lining powder (1.0g) and potassium hydroxide (11.2g, 0.2 mole, fused with 2 ml H2 O at 180° C) was stirred at 140°-150° C for 3 hours. The cooled mass was extracted with boiling petroleum (b.p. 62°-68° C), the resulting extracts were washed with dilute aqueous sodium hydroxide, water, dried, and then concentrated by evaporation. The product was distilled to give 2'-fluoro-4-isopropyldiphenyl ether, b.p. 106°-108° C/0.5mm. In a similar manner starting from the appropriate iodobenzene and alkylphenol the compounds set out in Table IV were obtained. With potassium hydroxide, copper Patent; The Boots Company Limited; US4036989; (1977); (A) English View in Reaxys

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Rx-ID: 26769241 View in Reaxys 806/1037 Yield

Conditions & References Kandil, K. S. A.; Holloway, C. E.; Clive, E.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1973); p. 1421 - 1423 ; (from Gmelin) View in Reaxys vol. Sn: Org.Verb.3; 1.1.4.5, page 89 - 91 ; (from Gmelin) View in Reaxys

Sn I

Rx-ID: 26366172 View in Reaxys 807/1037 Yield

Conditions & References in tetrachloromethane Davison; Rakita; Journal of Organometallic Chemistry; vol. 23; (1970); p. 407,410,411,415,419 ; (from Gmelin) View in Reaxys in tetrachloromethane vol. Sn: Org.Verb.3; 1.1.3.1, page 1 - 24 ; (from Gmelin) View in Reaxys

I H

HH (v3) H H H O (v3) H H Cr H (v6) O H H H H H H HH H H OH I

(v3)

Rx-ID: 26624934 View in Reaxys 808/1037 Yield

Conditions & References With water Sato, M.; Ishida, Y.; Nippon Kagaku Zasshi; vol. 91; (1970); p. 173 - 176 ; (from Gmelin) View in Reaxys in neat (no solvent), byproducts: C6H6, C6H5C6H5; heating; Sato, M.; Ishida, Y.; Nippon Kagaku Zasshi; vol. 91; (1970); p. 173 - 176 ; (from Gmelin) View in Reaxys in neat (no solvent), byproducts: C6H6, C6H5C6H5; heating; vol. Cr: Org.Verb.; 1.1.1.2.6, page 16 - 21 ; (from Gmelin) View in Reaxys With H2O vol. Cr: Org.Verb.; 1.1.1.2.6, page 16 - 21 ; (from Gmelin) View in Reaxys

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H HH H H

H SnI

HH H H H

H HH H

Rx-ID: 26769246 View in Reaxys 809/1037 Yield

Conditions & References in chloroform Seyferth; Journal of Organic Chemistry; vol. 22; (1957); p. 1599 View in Reaxys Rubinchik, G. F.; Manulkin, Z. M.; Zhurnal Obshchei Khimii; vol. 40; (1970); p. 123 - 126; Zhurnal Obshchei Khimii; vol. 40; (1970); p. 136 - 140 ; (from Gmelin) View in Reaxys in benzene Seyferth; Journal of Organic Chemistry; vol. 22; (1957); p. 1599 View in Reaxys Rubinchik, G. F.; Manulkin, Z. M.; Zhurnal Obshchei Khimii; vol. 40; (1970); p. 123 - 126; Zhurnal Obshchei Khimii; vol. 40; (1970); p. 136 - 140 ; (from Gmelin) View in Reaxys in benzene vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 ; (from Gmelin) View in Reaxys in chloroform vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 ; (from Gmelin) View in Reaxys

Rx-ID: 31255693 View in Reaxys 810/1037 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether in diethyl ether vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys Reaction Steps: 2 1: diethyl ether 2: benzene in diethyl ether, benzene Rubinchik, G. F.; Manulkin, Z. M.; Zhurnal Obshchei Khimii; vol. 40; (1970); p. 123 - 126; Zhurnal Obshchei Khimii; vol. 40; (1970); p. 136 - 140 View in Reaxys Reaction Steps: 4 1: diethyl ether 3: tetrahydrofuran 4: diethyl ether in tetrahydrofuran, diethyl ether

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vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys Reaction Steps: 4 1: diethyl ether 3: tetrahydrofuran 4: diethyl ether in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys

C 12H 10CrI 3.5

Rx-ID: 26529953 View in Reaxys 811/1037 Yield

Conditions & References by heating Mueller, H.; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 9; (1969); p. 311 - 312 View in Reaxys vol. Cr: Org.Verb.; 1.1.1.2, page 13 - 16 ; (from Gmelin) View in Reaxys

Sn I

Rx-ID: 26366920 View in Reaxys 812/1037 Yield

Conditions & References Srivastava, T. N.; Tandon, S. K.; Indian Journal of Applied Chemistry; vol. 26; (1963); p. 171 - 173 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.16.1.4.3, page 156 - 157 View in Reaxys Quan, M. Le; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 266; (1968); p. 832 - 833 ; (from Gmelin) View in Reaxys in further solvent(s), Kinetics, 88°C, BrCH2CH2Br solvent Flood, E. A.; Horvitz, L.; Journal of the American Chemical Society; vol. 55; (1933); p. 2534 - 2539 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.16.1.4.3, page 156 - 157 ; (from Gmelin) View in Reaxys

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Rx-ID: 26667445 View in Reaxys 813/1037 Yield

Conditions & References Kinetics Hunter,B.K.; Reeves,L.W.; Canadian Journal of Chemistry; vol. 46; (1968); p. 1399 - 1414 View in Reaxys Bott, R. W.; Eaborn, C.; Waters, J. A.; Journal of the Chemical Society; (1963); p. 681 - 689 View in Reaxys Bott, R. W.; Eaborn, C.; Waters, J. A.; Poc. Chem. Soc.; (1963); p. 51 - 51 ; (from Gmelin) View in Reaxys Kinetics vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 ; (from Gmelin) View in Reaxys

C– Cr 3+

Cr I

2 Na +

(v3)

Rx-ID: 26621650 View in Reaxys 814/1037 Yield

Conditions & References With iodine, byproducts: NaI Hein, F.; Weiss, R.; Naturwissenschaften; vol. 46; (1959); p. 321 - 322 ; (from Gmelin) View in Reaxys With I2, byproducts: NaI Hein, F.; Schmiedeknecht, K.; Journal of Organometallic Chemistry; vol. 5; (1966); p. 454 - 462 View in Reaxys vol. Cr: Org.Verb.; 1.1.1.2.8, page 22 - 23 ; (from Gmelin) View in Reaxys

Cl I

Rx-ID: 4041501 View in Reaxys 815/1037 Yield

Conditions & References With (dissociation) in acetic acid, T= 25 °C , Rate constant Jeffery,E.A. et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 617 - 620 View in Reaxys Reaction Steps: 2 1: NaOH-solution 2: 90 - 100 °C With sodium hydroxide Askenasy; Meyer,V.; Chemische Berichte; vol. 26; (1893); p. 1356 View in Reaxys Willgerodt; Chemische Berichte; vol. 25; (1892); p. 3495; Chemische Berichte; vol. 26; (1893); p. 357,1807 View in Reaxys

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I+

H O

Br–

Cu( 2+)

toluene-4-sulfonate

I I

Rx-ID: 7981018 View in Reaxys 816/1037 Yield

Conditions & References T= 100 °C , Product distribution Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys

I+

H O

Br–

copper (1+)

toluene-4-sulfonate

I I

Rx-ID: 7981019 View in Reaxys 817/1037 Yield

Conditions & References T= 100 °C , Product distribution Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys -1 F (v4)

B FF

Rx-ID: 7981225 View in Reaxys 818/1037 Yield

Conditions & References Quantum yield Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys

I+ F

O F

copper (II)-chloride

O O O

–

Rx-ID: 7981226 View in Reaxys 819/1037

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Yield

Conditions & References Quantum yield Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys

I+

H O

Br–

Cu( 2+)

toluene-4-sulfonate

HO I

Rx-ID: 8265195 View in Reaxys 820/1037 Yield

Conditions & References Product distribution Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys

I+

H O

Br–

copper (1+)

toluene-4-sulfonate

HO I

Rx-ID: 8265196 View in Reaxys 821/1037 Yield

Conditions & References Product distribution Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys

I+ H

aqueous fluoroboric acid

F–

aqueous dioxane I

aqueous acetonitrile O

Rx-ID: 8265201 View in Reaxys 822/1037 Yield

Conditions & References Quantum yield Caserio et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 336,337 View in Reaxys

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I+ Cl –

water

hydrochloric acid Rx-ID: 8277480 View in Reaxys 823/1037

Yield

Conditions & References T= 99 °C , auch unter Zusatz von Kupfer(II)-Salzen.Hydrolysis, Kinetics Beringer et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 342,347 View in Reaxys

Br+

O I–

platinum

Rx-ID: 8316844 View in Reaxys 824/1037 Yield

Conditions & References Nesmejanow et al.; Doklady Akademii Nauk SSSR; vol. 125; (1959); p. 330; ; 124-129<1959>203 View in Reaxys

Br+

O I–

silver

Rx-ID: 8316845 View in Reaxys 825/1037 Yield

Conditions & References Nesmejanow et al.; Doklady Akademii Nauk SSSR; vol. 125; (1959); p. 330; ; 124-129<1959>203 View in Reaxys

Br+ I–

copper

Rx-ID: 8425920 View in Reaxys 826/1037 Yield

Conditions & References Nesmejanow et al.; Doklady Akademii Nauk SSSR; vol. 125; (1959); p. 330; ; 124-129<1959>203 View in Reaxys

5 C–

Cr 3+

Li+

Rx-ID: 26621647 View in Reaxys 827/1037 Yield

Conditions & References With iodine Hein, F.; Weiss, R.; Naturwissenschaften; vol. 46; (1959); p. 321 - 322 ; (from Gmelin) View in Reaxys With I2 vol. Cr: Org.Verb.; 1.1.1.2.8, page 22 - 23 ; (from Gmelin) View in Reaxys

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S +I

I–

Rx-ID: 588980 View in Reaxys 828/1037 Yield

Conditions & References Erhitzen bis auf 160grad Beringer et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4279 View in Reaxys

I+

I–

Rx-ID: 698725 View in Reaxys 829/1037 Yield

Conditions & References T= 80 °C , Rate constant Beringer; Mausner; Journal of the American Chemical Society; vol. 80; (1958); p. 4535 View in Reaxys

I+

Br–

Rx-ID: 698726 View in Reaxys 830/1037 Yield

Conditions & References T= 80 °C , Rate constant Beringer; Mausner; Journal of the American Chemical Society; vol. 80; (1958); p. 4535 View in Reaxys

N I

I I

Rx-ID: 6673255 View in Reaxys 831/1037 Yield

Conditions & References Ford; Rust; Journal of the Chemical Society; (1958); p. 1297 View in Reaxys

F H

O +I

O–

sodium sulfite

F S

Rx-ID: 7977573 View in Reaxys 832/1037

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Yield

Conditions & References Beringer et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4279 View in Reaxys

Br+ I–

Rx-ID: 628781 View in Reaxys 833/1037 Yield

Conditions & References T= 21 °C Nesmejanow et al.; Tetrahedron; vol. 1; (1957); p. 145,156 View in Reaxys O

Rx-ID: 7442167 View in Reaxys 834/1037 Yield

Conditions & References T= 25 °C , Rate constant Keefer; Andrews; Journal of the American Chemical Society; vol. 79; (1957); p. 4348,4352 View in Reaxys T= 46 °C , Rate constant Keefer; Andrews; Journal of the American Chemical Society; vol. 79; (1957); p. 4348,4352 View in Reaxys T= 25 °C , Equilibrium constant Keefer; Andrews; Journal of the American Chemical Society; vol. 79; (1957); p. 4348,4352 View in Reaxys T= 46 °C , Equilibrium constant Keefer; Andrews; Journal of the American Chemical Society; vol. 79; (1957); p. 4348,4352 View in Reaxys

Sn I

Rx-ID: 26366461 View in Reaxys 835/1037 Yield

Conditions & References in diethyl ether, boiling, 8h; Seyferth, D.; Naturwissenschaften; vol. 44; (1957); p. 34 - 35 ; (from Gmelin) View in Reaxys in diethyl ether, boiling, 8h; Seyferth, D.; Journal of the American Chemical Society; vol. 79; (1957); p. 2133 - 2136 ; (from Gmelin) View in Reaxys in diethyl ether, boiling, 8h; vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 ; (from Gmelin)

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View in Reaxys Cl

Cl Sn

Rx-ID: 31256109 View in Reaxys 836/1037 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran 2: diethyl ether in tetrahydrofuran, diethyl ether Seyferth, D.; Journal of the American Chemical Society; vol. 79; (1957); p. 2133 - 2136 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran 2: diethyl ether in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran 2: diethyl ether in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys H

HH H H

Sn H

Br Mg

H SnI

HH H H H

H HH H

Rx-ID: 31296819 View in Reaxys 837/1037 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran 2: benzene in tetrahydrofuran, benzene Seyferth; Journal of Organic Chemistry; vol. 22; (1957); p. 1599 View in Reaxys

N+

I–

Rx-ID: 653749 View in Reaxys 838/1037

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Yield

Conditions & References Wittig; Polster; Justus Liebigs Annalen der Chemie; vol. 599; (1956); p. 13,20 View in Reaxys

I+ Cl –

Rx-ID: 698710 View in Reaxys 839/1037 Yield

Conditions & References T= 60 °C , Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 100 °C , Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 80 °C , Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 120 °C , Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys

I+ I–

Rx-ID: 698723 View in Reaxys 840/1037 Yield

Conditions & References T= 60 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 80 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 100 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys

I+

Br–

Rx-ID: 698724 View in Reaxys 841/1037 Yield

Conditions & References T= 60 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143

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View in Reaxys T= 100 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 120 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 80 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys

I+

Cl –

Rx-ID: 846557 View in Reaxys 842/1037 Yield

Conditions & References T= 98 °C , auch unter Zusatz von Kupfer(I)-chlorid, Kupfer(II)-chlorid und Wasser, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys O H

diphenyliodonium-nitrate

Rx-ID: 6585485 View in Reaxys 843/1037 Yield

Conditions & References T= 45 - 70 °C , Reaktion von Natriumphenolat, Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys Beringer; Gindler; Journal of the American Chemical Society; vol. 77; (1955); p. 3203 View in Reaxys O

steam

Rx-ID: 7172631 View in Reaxys 844/1037 Yield

Conditions & References Destillation Lucas; Kennedy; Organic Syntheses; vol. Coll. Vol. III; (1955); p. 485 View in Reaxys

N I

Rx-ID: 7442166 View in Reaxys 845/1037

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Yield

Conditions & References T= 25 °C , Equilibrium constant Keefer; Andrews; Journal of the American Chemical Society; vol. 80; (1955); p. 5350,5351, 5353 View in Reaxys T= 45 °C , Equilibrium constant Keefer; Andrews; Journal of the American Chemical Society; vol. 80; (1955); p. 5350,5351, 5353 View in Reaxys

Br–

+Mg

Rx-ID: 170832 View in Reaxys 846/1037 Yield

Conditions & References analoge Austausch-Reaktion mit weiteren Alkyl- und Arylmagnesiumhalogeniden Franzen; Chemische Berichte; vol. 87; (1954); p. 1148,1153 View in Reaxys

+Mg

Cl –

Rx-ID: 174298 View in Reaxys 847/1037 Yield

Conditions & References With diethyl ether Franzen; Chemische Berichte; vol. 87; (1954); p. 1148,1153 View in Reaxys

Br–

+Mg

Rx-ID: 174299 View in Reaxys 848/1037 Yield

Conditions & References With diethyl ether Franzen; Chemische Berichte; vol. 87; (1954); p. 1148,1153 View in Reaxys

Rx-ID: 847117 View in Reaxys 849/1037 Yield

Conditions & References With aluminium trichloride Woolf; Journal of the Chemical Society; (1954); p. 252,253, 257, 258 View in Reaxys

+Mg

Cl –

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ethynediyl dimagnesium dichloride Rx-ID: 7075925 View in Reaxys 850/1037

Yield

Conditions & References analoge Austausch-Reaktion mit weiteren Alkyl- und Arylmagnesiumhalogeniden Franzen; Chemische Berichte; vol. 87; (1954); p. 1148,1153 View in Reaxys

I+ Cl –

hydroxide

water

Rx-ID: 8265137 View in Reaxys 851/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys -1

F (v4)

B FF

hydroxide

water

I+

O I

Rx-ID: 8265138 View in Reaxys 852/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys

I+

-1 Cl

(v2)

hydroxide

water

Rx-ID: 8265139 View in Reaxys 853/1037 Yield

Conditions & References T= 59.1 °C , Rate constant

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Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys O– I+ HO

hydroxide

S OO

water

O I

Rx-ID: 8265140 View in Reaxys 854/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys O

N I+

O –O

hydroxide

water

O O

N O

Rx-ID: 8265141 View in Reaxys 855/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys

I+ I–

hydroxide

water

Rx-ID: 8265142 View in Reaxys 856/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys

I+ Br–

hydroxide

water

289/330

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Rx-ID: 8265143 View in Reaxys 857/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys -1 I+

Cl Hg

(v3)

hydroxide

water

Rx-ID: 8265144 View in Reaxys 858/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys

I+

O–

O N

hydroxide

water

Rx-ID: 8265145 View in Reaxys 859/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys O– I+

hydroxide

Cl O OO

water

O I

Rx-ID: 8265146 View in Reaxys 860/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys

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-1 Cl I+

hydroxide

(v4)

Sb ClCl

water

O I

Rx-ID: 8425918 View in Reaxys 861/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys -2 Cl I+

hydroxide

Cl SbCl Cl

water

O I

Rx-ID: 8425919 View in Reaxys 862/1037 Yield

Conditions & References T= 59.1 °C , Rate constant Levis; Stout; Journal of the American Chemical Society; vol. 76; (1954); p. 4619 View in Reaxys

iodine trichloride

Rx-ID: 6682806 View in Reaxys 863/1037 Yield

Conditions & References Campaigne; Leal; Journal of the American Chemical Society; vol. 75; (1953); p. 230 View in Reaxys

OH HO

S OO

H O

(v1)

-2

2 Ag+ (v1)

S OO

Rx-ID: 6585463 View in Reaxys 864/1037 Yield

Conditions & References Barker; Waters; Journal of the Chemical Society; (1952); p. 150,152 View in Reaxys

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-1 F (v4)

B FF

H N

H 2N

I+

Rx-ID: 711534 View in Reaxys 865/1037 Yield

Conditions & References Makarowa; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1951); p. 741,742; ; (1952); p. 7532 View in Reaxys

I I

Rx-ID: 359441 View in Reaxys 866/1037 Yield

Conditions & References T= -10 °C Wittig; Rieber; Justus Liebigs Annalen der Chemie; vol. 562; (1949); p. 187,190, 192 View in Reaxys

Rx-ID: 844395 View in Reaxys 867/1037 Yield

Conditions & References langsame Neutronen.Irradiation Glueckauf; Fay; Journal of the Chemical Society; (1936); p. 392 View in Reaxys Glueckauf; Jacobi; Kitt; Journal of the Chemical Society; (1949); p. Spl. 330, 332 View in Reaxys

Rx-ID: 6585457 View in Reaxys 868/1037 Yield

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I+ Cl –

N O

N N

Rx-ID: 19774 View in Reaxys 869/1037 Yield

Conditions & References Sandin; Brown; Journal of the American Chemical Society; vol. 69; (1947); p. 2253,2254 View in Reaxys

(v2)

Rx-ID: 762273 View in Reaxys 870/1037 Yield

Conditions & References With iodine Morton et al.; Journal of the American Chemical Society; vol. 69; (1947); p. 908,910 View in Reaxys With tetrachloromethane, Iodine monochloride Whitmore; Thorpe; Journal of the American Chemical Society; vol. 55; (1933); p. 782,783 View in Reaxys With water, Iodine monochloride Whitmore; Thorpe; Journal of the American Chemical Society; vol. 55; (1933); p. 782,783 View in Reaxys

phenylmercury acetate

Rx-ID: 6585476 View in Reaxys 871/1037 Yield

Conditions & References With iodine Morton et al.; Journal of the American Chemical Society; vol. 69; (1947); p. 908,910 View in Reaxys

phenylmercury nitrate

Rx-ID: 6585477 View in Reaxys 872/1037 Yield

Conditions & References With iodine, ethylene glycol, potassium iodide Morton et al.; Journal of the American Chemical Society; vol. 69; (1947); p. 908,910 View in Reaxys

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I+ Cl –

aqueous NaOH

N N

Rx-ID: 7977574 View in Reaxys 873/1037 Yield

Conditions & References Sandin; Brown; Journal of the American Chemical Society; vol. 69; (1947); p. 2253,2254 View in Reaxys

I+

HO SH

Cl –

neutral aqueous solution

Rx-ID: 7987399 View in Reaxys 874/1037 Yield

Conditions & References Sandin et al.; Journal of the American Chemical Society; vol. 69; (1947); p. 1550 View in Reaxys

I+

Cl –

water

O HO

Rx-ID: 7987400 View in Reaxys 875/1037 Yield

Conditions & References Sandin et al.; Journal of the American Chemical Society; vol. 69; (1947); p. 1550 View in Reaxys

O I

O O

Rx-ID: 26143334 View in Reaxys 876/1037 Yield

Conditions & References With sulfuric acid, educts = 27percent H2O2, 70percent H2SO4 Milas; Surgenor; Journal of the American Chemical Society; vol. 68; (1946); p. 642 View in Reaxys Milas, N. A.; Surgenor, D. M.; Journal of the American Chemical Society; vol. 68; (1946); p. 205 - 208 View in Reaxys Milas, N. A.; Surgenor, D. M.; Journal of the American Chemical Society; vol. 68; (1946); p. 643 - 644 ; (from Gmelin) View in Reaxys With H2SO4, educts = 27percent H2O2, 70percent H2SO4 vol. S: MVol.B2; 5, page 798 - 808 ; (from Gmelin) View in Reaxys

294/330

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O O I

Rx-ID: 273618 View in Reaxys 877/1037 Yield

Conditions & References Sandin; McCormack; Journal of the American Chemical Society; vol. 67; (1945); p. 2051 View in Reaxys

O O I

O O

meso-1.2-dibenzoyloxy-1.2-diphenyl-ethane Rx-ID: 7080610 View in Reaxys 878/1037

Yield

Conditions & References T= 80 °C Perret; Perrot; Helvetica Chimica Acta; vol. 28; (1945); p. 558,574 View in Reaxys

Cl O I

Cl O

meso-1.2-dibenzoyloxy-1.2-diphenyl-ethane Rx-ID: 7080611 View in Reaxys 879/1037

Yield

Conditions & References Perret; Perrot; Helvetica Chimica Acta; vol. 28; (1945); p. 558,574 View in Reaxys

O O I

O O

meso-1.2-dibenzoyloxy-1.2-diphenyl-ethane Rx-ID: 7080612 View in Reaxys 880/1037

Yield

Conditions & References Perret; Perrot; Helvetica Chimica Acta; vol. 28; (1945); p. 558,574 View in Reaxys

295/330

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-2 Cl

N+

(v4)

N Cl

Zn ClCl

methyl-phenyl-diazene Rx-ID: 8427146 View in Reaxys 881/1037

Yield

Conditions & References Hodgson; Marsden; Journal of the Chemical Society; (1945); p. 274 View in Reaxys

Rx-ID: 632086 View in Reaxys 882/1037 Yield

Conditions & References With iron(III) chloride Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

–O

Li+

Rx-ID: 635482 View in Reaxys 883/1037 Yield

Conditions & References Wittig; Harborth; Chemische Berichte; vol. 77/79; (1944); p. 306,311 View in Reaxys

I I

Rx-ID: 653656 View in Reaxys 884/1037 Yield

Conditions & References Wittig; Harborth; Chemische Berichte; vol. 77/79; (1944); p. 306,311 View in Reaxys

Cl I

(v3)

Rx-ID: 6585464 View in Reaxys 885/1037 Yield

Conditions & References T= 100 °C Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Rx-ID: 844396 View in Reaxys 886/1037

296/330

2018-06-17 20:31:40

Yield

Conditions & References T= 500 - 650 °C Schwarz; Pflugmacher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 205,219-223 View in Reaxys I

H O

Rx-ID: 7059439 View in Reaxys 887/1037 Yield

Conditions & References Wittig; Fuhrmann; Chemische Berichte; vol. 73; (1940); p. 1197,1217 View in Reaxys

Li O

3.3'-dimethoxy-biphenyl(?)

Rx-ID: 7059441 View in Reaxys 888/1037 Yield

Conditions & References anschliessende Behandlung mit Wasser Wittig; Fuhrmann; Chemische Berichte; vol. 73; (1940); p. 1197,1217 View in Reaxys O

H O

Rx-ID: 7439977 View in Reaxys 889/1037 Yield

Conditions & References Wittig; Fuhrmann; Chemische Berichte; vol. 73; (1940); p. 1197,1217 View in Reaxys

H O

Rx-ID: 7445024 View in Reaxys 890/1037

297/330

2018-06-17 20:31:40

Yield

Conditions & References Wittig; Fuhrmann; Chemische Berichte; vol. 73; (1940); p. 1197,1217 View in Reaxys

(v1)

I2Mg

Rx-ID: 26437206 View in Reaxys 891/1037 Yield

Conditions & References With hydrogenchloride, react. with MgI2, hydroylsis with dild. HCl; Bickley, E. A.; Gardner, J. H.; Journal of Organic Chemistry; vol. 5; (1940); p. 126 - 132 View in Reaxys vol. Ag: MVol.B5; 1.1.3, page 8 - 12 ; (from Gmelin) View in Reaxys

N N

I O

Rx-ID: 630951 View in Reaxys 892/1037 Yield

Conditions & References Waters; Journal of the Chemical Society; (1937); p. 113,116 View in Reaxys

N+

Cl –

Rx-ID: 631725 View in Reaxys 893/1037 Yield

Conditions & References Waters; Journal of the Chemical Society; (1937); p. 2007,2013 View in Reaxys

N N

Rx-ID: 841372 View in Reaxys 894/1037 Yield

Conditions & References Waters; Journal of the Chemical Society; (1937); p. 113,116 View in Reaxys

O I

Rx-ID: 5806754 View in Reaxys 895/1037 Yield

Conditions & References beim Erwaermen von Silberbenzoat Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

298/330

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O I

H 2N 2 O

Rx-ID: 5914109 View in Reaxys 896/1037 Yield

Conditions & References reagiert das Silber-Salz Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys O

N I

H 2N 2

Rx-ID: 5914125 View in Reaxys 897/1037 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

OH S OO

O N

Rx-ID: 6585465 View in Reaxys 898/1037 Yield

Conditions & References Varma; Sreenivasmurthyachar; Journal of the Indian Chemical Society; vol. 13; (1936); p. 187 View in Reaxys O

O N

Rx-ID: 6674423 View in Reaxys 899/1037 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

silver-<4-nitro benzoate>

O N

I O

Rx-ID: 6674424 View in Reaxys 900/1037

299/330

2018-06-17 20:31:40

Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

O I

H 2N 2 O

Rx-ID: 6682197 View in Reaxys 901/1037 Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

O I

m-toluic acid phenyl ester Rx-ID: 6729615 View in Reaxys 902/1037

Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys O

silver p-toluate

Rx-ID: 6819909 View in Reaxys 903/1037 Yield

Conditions & References With iodine Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys O Cl

silver-<4-chloro benzoate>

Rx-ID: 6821122 View in Reaxys 904/1037 Yield

Conditions & References With iodine, benzene Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

O I

H 2N 2

N O

Rx-ID: 7445528 View in Reaxys 905/1037

300/330

2018-06-17 20:31:40

Yield

Conditions & References Birckenbach; Meisenheimer; Chemische Berichte; vol. 69; (1936); p. 723,724 View in Reaxys

Br–

+Mg

Rx-ID: 304631 View in Reaxys 906/1037 Yield

Conditions & References Le Fevre; Markham; Journal of the Chemical Society; (1934); p. 703 View in Reaxys Melnikow; Zhurnal Obshchei Khimii; vol. 5; (1935); p. 28,29; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 2896 View in Reaxys

(v1)

OH S OO

-2

Hg 2+ (v1)

S OO

Rx-ID: 6674815 View in Reaxys 907/1037 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys

S OO

Hg2SO4

Rx-ID: 6674816 View in Reaxys 908/1037 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys

S OO

KIO3

Rx-ID: 6674817 View in Reaxys 909/1037 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 67; (1934); p. 917,920, 926 View in Reaxys

Ag+

2 (v1)

O–

O N O

Rx-ID: 26551924 View in Reaxys 910/1037 Yield

Conditions & References With copper(II) sulfate in water, react. with CuSO4 in H2O, addn. of I2; Challenger, E.; Richards, O. V.; Journal of the Chemical Society; (1934); p. 405 - 411 View in Reaxys vol. Ag: MVol.B5; 1.1.3, page 8 - 12 ; (from Gmelin)

301/330

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View in Reaxys

O H

H 2N

Rx-ID: 5802430 View in Reaxys 911/1037 Yield

Conditions & References Seide; Scherlin; Bras; Journal fuer Praktische Chemie (Leipzig); vol. <2>138; (1933); p. 225,228 View in Reaxys -1 (v1)

Ag+ Cl O

Rx-ID: 26083476 View in Reaxys 912/1037 Yield

Conditions & References in benzene Birckenbach, L.; Goubeau, J.; Ber. Dtsch. Chem. Ges.; vol. 65; (1932); p. 395 - 401 View in Reaxys Birckenbach, L.; Goubeau, J.; Ber. Dtsch. Chem. Ges.; vol. 66; (1933); p. 1280 - 1287 View in Reaxys vol. Ag: MVol.B1; 6.22.2.2.3, page 530 - 531 ; (from Gmelin) View in Reaxys

Cl Al

copper-salt

Rx-ID: 6585469 View in Reaxys 913/1037 Yield

Conditions & References Birckenbach; Goubeau; Berninger; Chemische Berichte; vol. 65; (1932); p. 1339,1343 View in Reaxys Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Cl Al

gold salt

Rx-ID: 6585471 View in Reaxys 914/1037 Yield

Cl Al

mercury-salt

Rx-ID: 6585475 View in Reaxys 915/1037 Yield

Conditions & References Birckenbach; Goubeau; Berninger; Chemische Berichte; vol. 65; (1932); p. 1339,1343 View in Reaxys

302/330

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Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Cl Al

silver-salt

Rx-ID: 6585478 View in Reaxys 916/1037 Yield

Rx-ID: 94194 View in Reaxys 917/1037 Yield

Conditions & References Zappi; Degiorgi; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 19; (1931); p. 83; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 21; (1933); p. 12 View in Reaxys Zappi; Degiorgi; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1035; Bulletin de la Societe Chimique de France; vol. 51; (1932); p. 1605 View in Reaxys

Cl I

2 Mg+

+Mg

Cl –

Rx-ID: 304625 View in Reaxys 918/1037 Yield

Conditions & References Zappi; Degiorgi; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 19; (1931); p. 162,164 View in Reaxys

Se+

I–

Rx-ID: 589305 View in Reaxys 919/1037 Yield

Conditions & References Erhitzen Leicester; Bergstrom; Journal of the American Chemical Society; vol. 53; (1931); p. 4428,4435 View in Reaxys

303/330

2018-06-17 20:31:40

Se I–

Se+

Rx-ID: 589329 View in Reaxys 920/1037 Yield

Conditions & References Pyrolysis Leicester; Bergstrom; Journal of the American Chemical Society; vol. 53; (1931); p. 4428,4435 View in Reaxys

Rx-ID: 693411 View in Reaxys 921/1037 Yield

Conditions & References Zappi; Deulofeu; Bulletin de la Societe Chimique de France; vol. <4> 47; (1930); p. 612 View in Reaxys

dipyridine-iodo(I)-perchlorate

Rx-ID: 6585470 View in Reaxys 922/1037 Yield

Conditions & References With trichloroacetic acid, T= 20 °C Patent; Carlsohn; DE692324; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 25; p. 126 View in Reaxys O O

Br–

+Mg

Rx-ID: 171533 View in Reaxys 923/1037 Yield

Conditions & References Gilman; Fothergill; Journal of the American Chemical Society; vol. 51; (1929); p. 3506 View in Reaxys

Se –

Se+

Rx-ID: 589274 View in Reaxys 924/1037 Yield

Conditions & References beim Erhitzen auf den Schmelzpunkt Leicester; Bergstrom; Journal of the American Chemical Society; vol. 51; (1929); p. 3589 View in Reaxys

304/330

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Br–

+Mg

toluene-sulfo iodide-(4)

Rx-ID: 6585480 View in Reaxys 925/1037 Yield

Conditions & References With diethyl ether Gilman; Fothergill; Journal of the American Chemical Society; vol. 51; (1929); p. 3506 View in Reaxys

Cl Sn

Rx-ID: 7977571 View in Reaxys 926/1037 Yield

Conditions & References Bost; Borgstrom; Journal of the American Chemical Society; vol. 51; (1929); p. 1924 View in Reaxys -1 I+

I Hg

(v3)

mercury (II)-iodide

Rx-ID: 8279850 View in Reaxys 927/1037 Yield

Conditions & References T= 180 - 200 °C Nesmejanow; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 178; (1929); p. 304; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 61; (1929); p. 1397 View in Reaxys -1 I

N+

mercury (II)-iodide

(v3)

Rx-ID: 8427078 View in Reaxys 928/1037 Yield

Conditions & References zersetzt Nesmejanow; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 178; (1929); p. 304; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 61; (1929); p. 1397 View in Reaxys 2

I–

N+

mercury (II)-iodide

HgI 2

Rx-ID: 8427079 View in Reaxys 929/1037 Yield

Conditions & References zersetzt Nesmejanow; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 178; (1929); p. 304; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 61; (1929); p. 1397

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View in Reaxys F F

O I

Ag+

F O–

F F

Rx-ID: 8540211 View in Reaxys 930/1037 Yield

Conditions & References Swarts; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 27; (1929); p. 683; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 1763 View in Reaxys

Rx-ID: 26382350 View in Reaxys 931/1037 Yield

Conditions & References in tetrachloromethane, 0°C Bost, R. W.; Borgstrom, P.; Journal of the American Chemical Society; vol. 51; (1929); p. 1922 - 1925 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.16.1.4.4, page 157 - 159 ; (from Gmelin) View in Reaxys

Rx-ID: 594256 View in Reaxys 932/1037 Yield

Conditions & References With chloroamine, diethyl ether Coleman; Hauser; Journal of the American Chemical Society; vol. 50; (1928); p. 1194 View in Reaxys With diethyl ether, oxygen Meisenheimer; Schlichenmaier; Chemische Berichte; vol. 61; (1928); p. 2043 View in Reaxys

Sn I

butyl-phenyl-benzyl tin iodide Rx-ID: 8270255 View in Reaxys 933/1037

306/330

2018-06-17 20:31:40

Yield

Conditions & References Kipping; Journal of the Chemical Society; (1928); p. 2370 View in Reaxys

Cl I

tribenzyl tin iodide

Rx-ID: 8289490 View in Reaxys 934/1037 Yield

Conditions & References Kipping; Journal of the Chemical Society; (1928); p. 2370 View in Reaxys

phenyl-tribenzyl stannane

iodine

I I Sn

Rx-ID: 8472970 View in Reaxys 935/1037 Yield

Conditions & References With tetrachloromethane Kipping; Journal of the Chemical Society; (1928); p. 2370 View in Reaxys

+Mg

I–

oxygen

Rx-ID: 8491246 View in Reaxys 936/1037 Yield

Conditions & References Product distribution Meisenheimer; Schlichenmaier; Chemische Berichte; vol. 61; (1928); p. 2043 View in Reaxys

O O I

quartz powder

307/330

2018-06-17 20:31:40

I HO

Rx-ID: 6683348 View in Reaxys 937/1037 Yield

Conditions & References T= 100 - 110 °C Wieland; Fischer; Justus Liebigs Annalen der Chemie; vol. 446; (1926); p. 63 View in Reaxys Reijnhart; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 71 View in Reaxys Erlenmeyer; Helvetica Chimica Acta; vol. 9; (1926); p. 820; Helvetica Chimica Acta; vol. 10; (1927); p. 625 View in Reaxys

Cl Sn

triphenyl tin iodide

Rx-ID: 8290034 View in Reaxys 938/1037 Yield

Conditions & References Bullard; Robinson; Journal of the American Chemical Society; vol. 49; (1927); p. 1371 View in Reaxys Chambers; Scherer; Journal of the American Chemical Society; vol. 48; (1926); p. 1057 View in Reaxys

Cl Sn

iodine (2 atomene)

triphenyl tin iodide Rx-ID: 8290035 View in Reaxys 939/1037

Yield

O +Ca

I–

Rx-ID: 609734 View in Reaxys 940/1037

308/330

2018-06-17 20:31:40

Yield

Conditions & References Gilman; Schulze; Journal of the American Chemical Society; vol. 48; (1926); p. 2466 View in Reaxys

O O

Rx-ID: 857564 View in Reaxys 941/1037 Yield

Conditions & References With iodine Erlenmeyer; Helvetica Chimica Acta; vol. 9; (1926); p. 820; Helvetica Chimica Acta; vol. 10; (1927); p. 625 View in Reaxys

Cl I

alkaline sodium arsenite

Rx-ID: 7155278 View in Reaxys 942/1037 Yield

Conditions & References Gutmann; Fresenius' Zeitschrift fuer Analytische Chemie; vol. 65; (1925); p. 250 View in Reaxys I O O

O N

Rx-ID: 7248476 View in Reaxys 943/1037 Yield

Conditions & References Vorlaender; Chemische Berichte; vol. 58; (1925); p. 1908 View in Reaxys I

O O

O N

O O

Rx-ID: 7248477 View in Reaxys 944/1037 Yield

Conditions & References Vorlaender; Chemische Berichte; vol. 58; (1925); p. 1908 View in Reaxys

I O

magnesium

Rx-ID: 7449719 View in Reaxys 945/1037 Yield

Conditions & References Zersetzung des Reaktionsprodukts mit Wasser Thomas; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 181; (1925); p. 219 View in Reaxys

309/330

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–O

2+I

(v1)

platinum-anode

Rx-ID: 7977572 View in Reaxys 946/1037 Yield

Conditions & References bei der elektrolytischen Oxydation Fichter; Lotter; Helvetica Chimica Acta; vol. 8; (1925); p. 441 View in Reaxys

I Sb O H

Rx-ID: 737238 View in Reaxys 947/1037 Yield

Conditions & References Wilkinson; Challenger; Journal of the Chemical Society; vol. 125; (1924); p. 860 View in Reaxys

benzenediazonium tetrachloro iodide

Rx-ID: 6585466 View in Reaxys 948/1037 Yield

Conditions & References With acetic acid, potassium iodide Chattaway; Garton; Parkes; Journal of the Chemical Society; vol. 125; (1924); p. 1984 View in Reaxys

iodine (1.4 mol)

phenyl bismuth diiodide Rx-ID: 8285020 View in Reaxys 949/1037

Yield

Conditions & References Wilkinson; Challenger; Journal of the Chemical Society; vol. 125; (1924); p. 858 View in Reaxys

310/330

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iodine (2 mol)

phenyl bismuth diiodide

bismuth triiodide Rx-ID: 8285021 View in Reaxys 950/1037

Yield

Conditions & References Wilkinson; Challenger; Journal of the Chemical Society; vol. 125; (1924); p. 858 View in Reaxys

iodine (0.7 mol)

phenyl bismuth diiodide

diphenyl bismuth iodide Rx-ID: 8285022 View in Reaxys 951/1037

Yield

Conditions & References Wilkinson; Challenger; Journal of the Chemical Society; vol. 125; (1924); p. 858 View in Reaxys

I O

petroleum ether

Rx-ID: 8469602 View in Reaxys 952/1037 Yield

Conditions & References Wilkinson; Challenger; Journal of the Chemical Society; vol. 125; (1924); p. 858 View in Reaxys

Cl –

Sb2+

Rx-ID: 93584 View in Reaxys 953/1037

311/330

2018-06-17 20:31:40

Yield

Conditions & References Challenger; Allpress; Journal of the Chemical Society; vol. 119; (1921); p. 916 View in Reaxys

Br–

+Mg

O I

Rx-ID: 170788 View in Reaxys 954/1037 Yield

Conditions & References Oddo; Binaghi; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 334 View in Reaxys

Cl I

Mg Br

Rx-ID: 171450 View in Reaxys 955/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Mg+

Br–

Rx-ID: 285926 View in Reaxys 956/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

O I

Mg Br

Rx-ID: 286608 View in Reaxys 957/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Cl I

Br–

Mg+

Rx-ID: 304628 View in Reaxys 958/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

I+ Cl I

Br– +Mg

Rx-ID: 304629 View in Reaxys 959/1037

312/330

2018-06-17 20:31:40

Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Mg Br

Rx-ID: 749885 View in Reaxys 960/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Br–

+Mg

O I+

Rx-ID: 749886 View in Reaxys 961/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys Cl I

magnesium

Rx-ID: 7449725 View in Reaxys 962/1037 Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Br–

diphenyliodonium hydroxide Rx-ID: 8426632 View in Reaxys 963/1037

Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Cl I

Br–

+Mg

diphenyliodonium hydroxide Rx-ID: 8426633 View in Reaxys 964/1037

313/330

2018-06-17 20:31:40

Yield

Conditions & References Hepworth; Journal of the Chemical Society; vol. 119; (1921); p. 1255 View in Reaxys

Br–

+Mg

triphenylmethane and 1,1,2,2-tetraphenyl-ethane Rx-ID: 8428198 View in Reaxys 965/1037

Yield

Conditions & References Oddo; Binaghi; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 334 View in Reaxys

F I

Br–

+Mg

Rx-ID: 171013 View in Reaxys 966/1037 Yield

Conditions & References Zersetzen des Reaktionsproduktes mit Wasser; Produkt5: Stilben Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys

Br–

+Mg

iodine

Rx-ID: 8316869 View in Reaxys 967/1037 Yield

Conditions & References Datta; Mitter; Journal of the American Chemical Society; vol. 41; (1919); p. 291 View in Reaxys

O I

trinitrophenol

Rx-ID: 6731959 View in Reaxys 968/1037 Yield

Conditions & References Datta; Chatterjee; Journal of the American Chemical Society; vol. 39; (1917); p. 437 View in Reaxys

Br–

+Mg

Rx-ID: 173533 View in Reaxys 969/1037 Yield

Conditions & References With diethyl ether Grignard; Bellet; Courtot; Annales de Chimie (Cachan, France); vol. <9> 4; (1915); p. 47 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 389

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View in Reaxys

Br–

+Mg

Rx-ID: 173534 View in Reaxys 970/1037 Yield

Conditions & References Grignard; Bellet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 458 View in Reaxys Grignard; Bellet; Courtot; Annales de Chimie (Cachan, France); vol. <9> 4; (1915); p. 47 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 389 View in Reaxys

iodo monobromideide

diphenyl bismuth bromide Rx-ID: 8275290 View in Reaxys 971/1037

Yield

Conditions & References Challenger; Allpress; Journal of the Chemical Society; vol. 107; (1915); p. 23 View in Reaxys

diphenyl bismuth iodide Rx-ID: 8275296 View in Reaxys 972/1037

Yield

Conditions & References Challenger; Allpress; Journal of the Chemical Society; vol. 107; (1915); p. 23 View in Reaxys

(v2)

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mercury iodide

Rx-ID: 8279872 View in Reaxys 973/1037 Yield

Conditions & References bei laengerem Kochen Hilpert; Gruettner; Chemische Berichte; vol. 47; (1914); p. 184 View in Reaxys

δ.δ-dichloro-acetoacetic acid ethyl ester

Rx-ID: 5442319 View in Reaxys 974/1037 Yield

Conditions & References T= 60 - 80 °C Sachs; Monatshefte fuer Chemie; vol. 34; (1913); p. 1410 View in Reaxys Sachs; Monatshefte fuer Chemie; vol. 34; (1913); p. 1410 View in Reaxys

O I

sodium persulfate

Rx-ID: 6674818 View in Reaxys 975/1037 Yield

Conditions & References Elbs; Jaroslawzew; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 92 View in Reaxys

carbon monoxide

Rx-ID: 7451848 View in Reaxys 976/1037 Yield

Conditions & References T= 500 °C , p= 15 - 25Torr Staudinger; Anthes; Chemische Berichte; vol. 46; (1913); p. 1435 View in Reaxys

N I

Br–

+Mg

Rx-ID: 218292 View in Reaxys 977/1037 Yield

Conditions & References v. Braun; Deutsch; Schmatloch; Chemische Berichte; vol. 45; (1912); p. 1255 View in Reaxys

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I–

I+

Rx-ID: 545416 View in Reaxys 978/1037 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Willgerodt; Hilgenberg; Chemische Berichte; vol. 42; (1909); p. 3827 View in Reaxys

Na +

I Cl

O–

O– O

sodium chloride O

Rx-ID: 7457890 View in Reaxys 979/1037 Yield

Conditions & References Hodgson; Journal of the Chemical Society; vol. 96 I; (1909); p. 18; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 738 View in Reaxys F

Rx-ID: 8211580 View in Reaxys 980/1037 Yield

Conditions & References Weinland; Reischle; ; vol. 60; (1908); p. 170 View in Reaxys

N N

N+

Rx-ID: 840241 View in Reaxys 981/1037 Yield

Conditions & References T= -10 - -5 °C , beim Behandeln von Silber-benzol-isodiazotat unter Lichtabschluss Bamberger; Chemische Berichte; vol. 28; (1895); p. 248; Chemische Berichte; vol. 27; (1894); p. 1348 View in Reaxys Euler; Chemische Berichte; vol. 36; (1903); p. 2505 View in Reaxys Bamberger; Chemische Berichte; vol. 27; (1894); p. 917; Chemische Berichte; vol. 28; (1895); p. 227 View in Reaxys

N N

silver benzene isodiazotate

Rx-ID: 6997208 View in Reaxys 982/1037

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Yield

Conditions & References With diethyl ether, T= -10 - -5 °C Euler; Chemische Berichte; vol. 36; (1903); p. 2505 View in Reaxys Bamberger; Chemische Berichte; vol. 27; (1894); p. 917; Chemische Berichte; vol. 28; (1895); p. 227 View in Reaxys

N N

silver benzene-standard diazotate

Rx-ID: 6997209 View in Reaxys 983/1037 Yield

Conditions & References With diethyl ether, T= -10 - -5 °C Bamberger; Chemische Berichte; vol. 28; (1895); p. 248; Chemische Berichte; vol. 27; (1894); p. 1348 View in Reaxys Hantzsch; Chemische Berichte; vol. 36; (1903); p. 3099 Anm. View in Reaxys Hantzsch; Reddelien; View in Reaxys

Br–

+Mg

Rx-ID: 624356 View in Reaxys 984/1037 Yield

Conditions & References With diethyl ether, iodine Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 135; (1902); p. 1350 View in Reaxys

Br–

+Mg

iodine

Rx-ID: 8316842 View in Reaxys 985/1037 Yield

Conditions & References Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 135; (1902); p. 1350 View in Reaxys

Br–

+Mg

iodine

Rx-ID: 8316843 View in Reaxys 986/1037 Yield

Conditions & References Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 135; (1902); p. 1350 View in Reaxys F

Rx-ID: 7915881 View in Reaxys 987/1037 Yield

Conditions & References durch Feuchtigkeit

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Weinland; Stille; Chemische Berichte; vol. 34; (1901); p. 2632; Justus Liebigs Annalen der Chemie; vol. 328; (1903); p. 135 View in Reaxys O–

O N

N+

Rx-ID: 543923 View in Reaxys 988/1037 Yield

Conditions & References With hydrogen iodide Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2540 View in Reaxys

O– 2 N+ N

–O

S OO

Rx-ID: 595684 View in Reaxys 989/1037 Yield

O N

iodosulfur

Rx-ID: 6585472 View in Reaxys 990/1037 Yield

Conditions & References Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys

N+

water

Rx-ID: 6585482 View in Reaxys 991/1037 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2540 View in Reaxys beim Behandeln von Benzoldiazoniumnitrat Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2540 View in Reaxys

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N+

water

Rx-ID: 6585483 View in Reaxys 992/1037 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2540 View in Reaxys Knoevenagel; Chemische Berichte; vol. 23; (1890); p. 2996 View in Reaxys

(v2)

Hg Cl

(v2)

Rx-ID: 304626 View in Reaxys 993/1037 Yield

Conditions & References Willgerodt; Chemische Berichte; vol. 31; (1898); p. 921 View in Reaxys

Rx-ID: 7155275 View in Reaxys 994/1037 Yield

Conditions & References Willgerodt; Chemische Berichte; vol. 29; (1896); p. 1569 View in Reaxys HO S

Rx-ID: 7155276 View in Reaxys 995/1037 Yield

Conditions & References Hartmann; Meyer,V.; Chemische Berichte; vol. 27; (1894); p. 505 Anm. View in Reaxys

HO S

Rx-ID: 7155277 View in Reaxys 996/1037 Yield

Conditions & References Hartmann; Meyer,V.; Chemische Berichte; vol. 27; (1894); p. 505 Anm. View in Reaxys

H O

diphenyliodonium hydroxide

Rx-ID: 8540263 View in Reaxys 997/1037 Yield

Conditions & References Willgerodt; Chemische Berichte; vol. 26; (1893); p. 358,1307 View in Reaxys Hartmann; Meyer,V.; Chemische Berichte; vol. 27; (1894); p. 1593,1598 View in Reaxys

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Rx-ID: 285928 View in Reaxys 998/1037 Yield

Conditions & References With water Willgerodt; Chemische Berichte; vol. 26; (1893); p. 358,1307 View in Reaxys T= 90 - 100 °C Askenasy; Meyer,V.; Chemische Berichte; vol. 26; (1893); p. 1356 View in Reaxys Willgerodt; Chemische Berichte; vol. 25; (1892); p. 3495; Chemische Berichte; vol. 26; (1893); p. 357,1807 View in Reaxys

O I

aqueous chromic acid solution

Rx-ID: 7155279 View in Reaxys 999/1037 Yield

Conditions & References Willgerodt; Chemische Berichte; vol. 26; (1893); p. 1309 View in Reaxys

H I

Rx-ID: 7441638 View in Reaxys 1000/1037 Yield

Conditions & References Willgerodt; Chemische Berichte; vol. 26; (1893); p. 362; Journal fuer Praktische Chemie (Leipzig); vol. <2> 33; (1886); p. 160 View in Reaxys

O O

oxygen

Rx-ID: 7456701 View in Reaxys 1001/1037 Yield

Conditions & References Willgerodt; Chemische Berichte; vol. 26; (1893); p. 1309 View in Reaxys

N+

Rx-ID: 840242 View in Reaxys 1002/1037 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Oddo; Gazzetta Chimica Italiana; vol. 20; (1890); p. 639 View in Reaxys Kekule; View in Reaxys

N+

Cl –

Rx-ID: 844158 View in Reaxys 1003/1037

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Yield

Conditions & References With zinc copper Oddo; Gazzetta Chimica Italiana; vol. 20; (1890); p. 639 View in Reaxys

N+

zinc copper

Rx-ID: 6585484 View in Reaxys 1004/1037 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Oddo; Gazzetta Chimica Italiana; vol. 20; (1890); p. 639 View in Reaxys

HN H 2N

Rx-ID: 724324 View in Reaxys 1005/1037 Yield

Conditions & References With water, iodine, potassium iodide v. Meyer,E.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 36; (1887); p. 115 View in Reaxys

OH HO

S OO

Rx-ID: 6585458 View in Reaxys 1006/1037 Yield

Conditions & References T= 150 °C Neumann; Justus Liebigs Annalen der Chemie; vol. 241; (1887); p. 84 View in Reaxys

OH I

Rx-ID: 190073 View in Reaxys 1007/1037 Yield

Conditions & References Willgerodt; Journal fuer Praktische Chemie (Leipzig); vol. <2> 33; (1886); p. 155; Chem. Zentralbl.; vol. 56; (1885); p. 835 View in Reaxys

Rx-ID: 844163 View in Reaxys 1008/1037 Yield

Conditions & References T= 200 °C

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Michaelis; Reese; Justus Liebigs Annalen der Chemie; vol. 233; (1886); p. 43 View in Reaxys

benzenediazopiperidide

Rx-ID: 6585467 View in Reaxys 1009/1037 Yield

Conditions & References With hydrogen iodide Wallach; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 242 View in Reaxys

Cl I

(v3)

Rx-ID: 6585460 View in Reaxys 1010/1037 Yield

Conditions & References Meyer,L.; Justus Liebigs Annalen der Chemie; vol. 231; (1885); p. 195; Journal fuer Praktische Chemie (Leipzig); vol. <2> 34; (1886); p. 504 View in Reaxys

N+

acid

Rx-ID: 6585474 View in Reaxys 1011/1037 Yield

Conditions & References beim Behandeln von Benzoldiazoniumchlorid Sandmeyer; Chemische Berichte; vol. 17; (1884); p. 1634 View in Reaxys

Cl Al

Rx-ID: 6585459 View in Reaxys 1012/1037 Yield

Conditions & References Greene; Bulletin de la Societe Chimique de France; vol. <2> 36; (1881); p. 234 View in Reaxys

Sn I

Rx-ID: 8251552 View in Reaxys 1013/1037 Yield

Conditions & References Ladenburg; Justus Liebigs Annalen der Chemie; vol. 159; (1871); p. 253 View in Reaxys

(v2) I

mercury iodide Rx-ID: 6215655 View in Reaxys 1014/1037

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Yield

Conditions & References Dreher; Otto; Justus Liebigs Annalen der Chemie; vol. 154; (1870); p. 94 View in Reaxys

(v2) I

phenylmercury iodide Rx-ID: 6218458 View in Reaxys 1015/1037

Yield

Conditions & References Dreher; Otto; Justus Liebigs Annalen der Chemie; vol. 154; (1870); p. 94 View in Reaxys

O H

H O

Rx-ID: 6585461 View in Reaxys 1016/1037 Yield

Conditions & References T= 200 - 240 °C Kekule; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 167 View in Reaxys

diiodobenzene; triiodobenzene

Rx-ID: 6727889 View in Reaxys 1017/1037 Yield

Conditions & References With iodine, iodic acid, T= 200 - 240 °C Kekule; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 167 View in Reaxys

OH HO

KIO3

S OO

Rx-ID: 6585473 View in Reaxys 1018/1037 Yield

Conditions & References Peltzer; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 201 View in Reaxys

O Na +

O–

Rx-ID: 532609 View in Reaxys 1019/1037 Yield

Conditions & References With Iodine monochloride Schuetzenberger; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1861); p. 349; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1862); p. 251 View in Reaxys

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-1 N+

(v2)

Rx-ID: 628792 View in Reaxys 1020/1037 Yield

Conditions & References es erfolgt Zersetzung Patent; Froehlich; DE87970; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 4; p. 1102 View in Reaxys

H I

nitrogen

H 2N

Rx-ID: 6217155 View in Reaxys 1021/1037 Yield

Conditions & References v. Meyer; Journal fuer Praktische Chemie (Leipzig); vol. <2> 36; p. 115 View in Reaxys

O H 2N

5C6H8N2+3HI

nitrogen

Rx-ID: 6217262 View in Reaxys 1022/1037 Yield

Conditions & References Lockemann; Weiniger; Chemische Berichte; vol. 41; p. 3103 View in Reaxys -2 (v1)

(v1)

Cu 2+

S O

copper

nitrogen

H 2N

Rx-ID: 6217294 View in Reaxys 1023/1037 Yield

Conditions & References Gattermann; Hoelzle; Chemische Berichte; vol. 25; p. 1075 View in Reaxys Cl

I Br

Rx-ID: 31255654 View in Reaxys 1024/1037 Yield

Conditions & References Reaction Steps: 4 1: diethyl ether 3: Na / petroleum ether With Na in diethyl ether vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys

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Rx-ID: 31255668 View in Reaxys 1025/1037 Yield

Conditions & References Reaction Steps: 4 1: diethyl ether 3: Na / petroleum ether With Na in diethyl ether vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys

Rx-ID: 31255990 View in Reaxys 1026/1037 Yield

Conditions & References Reaction Steps: 3 2: Na / petroleum ether With Na in petroleum ether vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys

Rx-ID: 31256026 View in Reaxys 1027/1037 Yield

Conditions & References Reaction Steps: 3 2: Na / petroleum ether With Na in petroleum ether vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys

Sn I

Rx-ID: 31296783 View in Reaxys 1028/1037 Yield

Conditions & References Reaction Steps: 2 1: Zn-Cu / tetrahydrofuran 2: tetrachloromethane With Zn-Cu in tetrahydrofuran, tetrachloromethane vol. Sn: Org.Verb.3; 1.1.3.1, page 1 - 24 View in Reaxys

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Sn I

Rx-ID: 31296814 View in Reaxys 1029/1037 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: tetrachloromethane in tetrachloromethane, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.1, page 1 - 24 View in Reaxys

Mg Sn I

Rx-ID: 31296852 View in Reaxys 1030/1037 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether in diethyl ether vol. Sn: Org.Verb.3; 1.1.4.5, page 89 - 91 View in Reaxys H

HH H H

Sn H

H SnI

HH H

H HH

H H

Rx-ID: 31296947 View in Reaxys 1031/1037 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran 2: chloroform in tetrahydrofuran, chloroform vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys

O Sn

Rx-ID: 31297006 View in Reaxys 1032/1037 Yield

Conditions & References Reaction Steps: 3 2: tetrahydrofuran 3: diethyl ether

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in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys Reaction Steps: 3 2: tetrahydrofuran 3: diethyl ether in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys

H HH H H

O H

H HH H

H SnI

H H

H HH H

Rx-ID: 31297007 View in Reaxys 1033/1037 Yield

Conditions & References Reaction Steps: 3 2: tetrahydrofuran 3: chloroform in tetrahydrofuran, chloroform vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys

Rx-ID: 31297048 View in Reaxys 1034/1037 Yield

Conditions & References Reaction Steps: 3 1: succinimide / ethanol 2: tetrahydrofuran 3: diethyl ether With succinimide in tetrahydrofuran, diethyl ether, ethanol vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys Reaction Steps: 3 1: succinimide / ethanol 2: tetrahydrofuran 3: diethyl ether With succinimide in tetrahydrofuran, diethyl ether, ethanol vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys

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H HH H H

H SnI

HH H H H

H HH H

Rx-ID: 31297049 View in Reaxys 1035/1037 Yield

Conditions & References Reaction Steps: 3 1: succinimide / ethanol 2: tetrahydrofuran 3: chloroform With succinimide in tetrahydrofuran, ethanol, chloroform vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys H

H H

I H

Rx-ID: 31297084 View in Reaxys 1036/1037 Yield

Conditions & References Reaction Steps: 3 2: tetrahydrofuran 3: diethyl ether in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys Reaction Steps: 3 2: tetrahydrofuran 3: diethyl ether in tetrahydrofuran, diethyl ether vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys H

HH H H

I H

H SnI

HH H H H

H HH H

Rx-ID: 31297085 View in Reaxys 1037/1037 Yield

Conditions & References Reaction Steps: 3 2: tetrahydrofuran 3: chloroform in tetrahydrofuran, chloroform

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vol. Sn: Org.Verb.3; 1.1.3.6, page 57 - 68 View in Reaxys

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