Query Query
Results
Date
27 reactions in Reaxys
2016-07-07 14h:36m:21s (EST)
27 reactions in Reaxys
2016-07-07 14h:37m:14s (EST)
O
1. Query O
Search as: As drawn, No mixtures, No charges, No radicals 2. Query
(1. Query) AND itemno in (1)
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OH
O
O
O
O
Rx-ID: 9417884 View in Reaxys 1/27 Yield
Conditions & References
74 %
With lithium trifluoromethane sulfonate in toluene, Time= 5h, T= 110 °C Datta, Swarup; Chang, Chia-Lung; Yeh, Kuo-Liang; Liu, Rai-Shung; Journal of the American Chemical Society; vol. 125; nb. 31; (2003); p. 9294 - 9295 View in Reaxys
O
O
O
O
O
HO
O
Rx-ID: 39588098 View in Reaxys 2/27 Yield
Conditions & References
80 %
General procedure Nafion-H (14.65 g, 10 percent wt. percent based on the 1,2-methylene-dioxybenzene was used) was added to the mixture of 1,2-methylenedioxybenzene (146.54 g, 1.2 mol) and allyl alcohol (2.33 g, 0.04 mol) and stirred at room temperature until the allyl alcohol is disappeared. The Nafion-H catalyst was filtered off. Excess 1,2-methylenedioxybenzene was removed under reduced pressure. The crude product was vacuum distilled, 5.19 g of safrole, boiling at 120-130 °C (10-15 mm Hg), was obtained. Colourless and typically smelling oil. Total yield (from the allyl alcohol), 80 percent of theory. With Nafion-H resin, T= 20 °C , Friedel-Crafts Alkylation Ou, Wenhua; Huang, Hong; Asian Journal of Chemistry; vol. 27; nb. 3; (2015); p. 1175 - 1176 View in Reaxys
Br Br
O
O
O
O
Rx-ID: 1869601 View in Reaxys 3/27 Yield
Conditions & References
95 %
With (2-((dimethylamino)methyl)phenyl)dimethyltin in tetrahydrofuran, T= 20 °C Vedejs, E.; Duncan, S. M.; Haight, A. R.; Journal of Organic Chemistry; vol. 58; nb. 11; (1993); p. 3046 - 3050 View in Reaxys OH
Si
O
O
O
O
Rx-ID: 2557648 View in Reaxys 4/27 Yield 43 %
Conditions & References With BF3*AcOH in dichloromethane, Time= 0.0833333h, T= 25 °C Wilson, Stephen R.; Shedrinsky, Alexander; Journal of Organic Chemistry; vol. 47; nb. 10; (1982); p. 1983 - 1984 View in Reaxys
OH HO
B
O
Br
O
O O
Rx-ID: 38051863 View in Reaxys 5/27
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Yield
Conditions & References
86 %
With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I), caesium carbonate in acetonitrile, Time= 18h, T= 65 °C , chemoselective reaction Levin, Mark D.; Toste, F. Dean; Angewandte Chemie - International Edition; vol. 53; nb. 24; (2014); p. 6211 - 6215; Angew. Chem.; vol. 126; nb. 24; (2014); p. 6325 - 6329,5 View in Reaxys
Cl
O
O
Si O
O
Rx-ID: 10279727 View in Reaxys 6/27 Yield
Conditions & References
77 %
With caesium carbonate in 2,2,2-trifluoroethanol, Time= 14h, Irradiation Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; Organic and Biomolecular Chemistry; vol. 3; nb. 15; (2005); p. 2868 - 2871 View in Reaxys O
O S
O
O
O O
O
Rx-ID: 9299462 View in Reaxys 7/27 Yield
Conditions & References
45 % Chromat.
With {(norbornadiene)rhodium(I)(NCCH3)2}(PF6) in toluene, Time= 15h, T= 0 °C Tsukada, Naofumi; Yagura, Yasushige; Sato, Tetsuo; Inoue, Yoshio; Synlett; nb. 10; (2003); p. 1431 - 1434 View in Reaxys
O
O
O
O
O
Rx-ID: 21236477 View in Reaxys 8/27 Yield
Conditions & References Reaction Steps: 2 1: 1.) tert-BuLi / 1.) -78 deg C, 2.) ether, -78 deg C 2: 43 percent / BF3*AcOH / CH2Cl2 / 0.08 h / 25 °C With tert.-butyl lithium, BF3*AcOH in dichloromethane Wilson, Stephen R.; Shedrinsky, Alexander; Journal of Organic Chemistry; vol. 47; nb. 10; (1982); p. 1983 - 1984 View in Reaxys
Br
O
Br
O
O O
Rx-ID: 37794102 View in Reaxys 9/27 Yield
Conditions & References Stage 1: With magnesium in tetrahydrofuran Stage 2: With ammonium chloride in water Chen, Huoji; Yang, Wanfei; Wu, Wanqing; Jiang, Huanfeng; Organic and Biomolecular Chemistry; vol. 12; nb. 21; (2014); p. 3340 - 3343 View in Reaxys Stage 1: With iodine, magnesium in tetrahydrofuran Stage 2: in tetrahydrofuran, Time= 1h
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Stage 3: With ammonium chloride in tetrahydrofuran, water Jiang, Huanfeng; Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Wu, Wanqing; Chemical Communications; vol. 50; nb. 54; (2014); p. 7202 - 7204 View in Reaxys
E
Br
O
O
O
O
E
O O
Rx-ID: 39899194 View in Reaxys 10/27 Yield
Conditions & References With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide, lithium tri-t-butoxyaluminum hydride in tetrahydrofuran, toluene, Time= 16h, T= 90 °C Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295 View in Reaxys
Br
O
O
O
O
O
O
Rx-ID: 40125710 View in Reaxys 11/27 Yield
Conditions & References Stage 1: With magnesium, lithium chloride in tetrahydrofuran, Time= 2h, T= 20 °C , Inert atmosphere Stage 2: With iron (III) acetylacetonate in tetrahydrofuran, Time= 0.0833333h, Inert atmosphere Stage 3: in tetrahydrofuran, Time= 0.75h, T= 0 °C , Inert atmosphere Bagal, Dattatraya B.; Kachkovskyi, Georgiy; Knorn, Matthias; Rawner, Thomas; Bhanage, Bhalchandra M.; Reiser, Oliver; Angewandte Chemie - International Edition; vol. 54; nb. 24; (2015); p. 6999 - 7002; Angew. Chem.; vol. 127; nb. 24; (2015) View in Reaxys
O O
HO O O
O
O
O
O
O
O O
O
Rx-ID: 3197078 View in Reaxys 12/27 Yield
Conditions & References
0.2 g, 90 With sodium tetrahydroborate in methanol, Time= 1h, Ambient temperature, Further byproducts given mg, 0.11 g, yakushijin k.; tohshima t.; kitagawa e.; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 11 175 mg 22 View in Reaxys 0.2 g, 175 With sodium tetrahydroborate in methanol, Time= 1h, Ambient temperature, Further byproducts given mg, 0.11 g, yakushijin k.; tohshima t.; kitagawa e.; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 11 90 mg 22 View in Reaxys 0.11 g, 90 mg, 175 mg, 0.2 g
With sodium tetrahydroborate in methanol, Time= 1h, Ambient temperature, Further byproducts given yakushijin k.; tohshima t.; kitagawa e.; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 11 22 View in Reaxys
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0.2 g, 175 With sodium tetrahydroborate in methanol, Time= 1h, Ambient temperature, Further byproducts given mg, 90 mg, yakushijin k.; tohshima t.; kitagawa e.; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 11 0.11 g 22 View in Reaxys
Br
O
O
O
O
Rx-ID: 40937679 View in Reaxys 13/27 Yield
Conditions & References Reaction Steps: 2 1: iodine / tetrahydrofuran / 20 °C 2: tetrahydrofuran / 1 h With iodine in tetrahydrofuran Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578 View in Reaxys O O
E
O
O
O
O
E
O O
Rx-ID: 39899114 View in Reaxys 14/27 Yield
Conditions & References Reaction Steps: 3 1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 °C 2: phosphorus tribromide / diethyl ether / 1 h / |Cooling with ice 3: 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide; lithium tri-t-butoxyaluminum hydride / toluene; tetrahydrofuran / 16 h / 90 °C With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide, phosphorus tribromide, diisobutylaluminium hydride, lithium tri-t-butoxyaluminum hydride in tetrahydrofuran, diethyl ether, hexane, toluene Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295 View in Reaxys
HO
E
O
O
O
O
E
O O
Rx-ID: 39899168 View in Reaxys 15/27 Yield
Conditions & References Reaction Steps: 2 1: phosphorus tribromide / diethyl ether / 1 h / |Cooling with ice 2: 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide; lithium tri-t-butoxyaluminum hydride / toluene; tetrahydrofuran / 16 h / 90 °C With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide, phosphorus tribromide, lithium tri-t-butoxyaluminum hydride in tetrahydrofuran, diethyl ether, toluene Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O
O
O
O
E
O O
Rx-ID: 39899215 View in Reaxys 16/27 Yield
Conditions & References Reaction Steps: 4 1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 2: diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / -78 °C 3: phosphorus tribromide / diethyl ether / 1 h / |Cooling with ice 4: 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide; lithium tri-t-butoxyaluminum hydride / toluene; tetrahydrofuran / 16 h / 90 °C With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide, phosphorus tribromide, sodium hydride, diisobutylaluminium hydride, lithium tri-t-butoxyaluminum hydride in tetrahydrofuran, diethyl ether, hexane, toluene, mineral oil Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.; Journal of the American Chemical Society; vol. 137; nb. 16; (2015); p. 5292 - 5295 View in Reaxys
Cl
O
O
O
O
O
Si O
Rx-ID: 42219488 View in Reaxys 17/27 Yield
Conditions & References
50 %, 10 in water, acetonitrile, Time= 6.25h, Irradiation, Flow reactor %Chromat. Bergami, Matteo; Protti, Stefano; Ravelli, Davide; Fagnoni, Maurizio; Advanced Synthesis and Catalysis; vol. 358; nb. 7; (2016); p. 1164 - 1172 View in Reaxys
O O
HO O O
O
O
O
O
O
O
O
O
Rx-ID: 3197079 View in Reaxys 18/27 Yield
Conditions & References
0.2 g, 175 With sodium tetrahydroborate in methanol, Time= 1h, Ambient temperature, Further byproducts given mg, 0.11 g, yakushijin k.; tohshima t.; kitagawa e.; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 11 60 mg 22 View in Reaxys
3,4-methylenedioxy-trans(?)-cinnamyl alcohol
O
O
O
O
Rx-ID: 5706801 View in Reaxys 19/27 Yield
Conditions & References With aluminum oxide, lithium aluminium tetrahydride, diethyl ether Birch; Slaytor; Chemistry and Industry (London, United Kingdom); (1956); p. 1524 View in Reaxys
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I
I
OH
O
OH
O
Rx-ID: 170702 View in Reaxys 20/27 Yield
Conditions & References With potassium carbonate, acetone Perkin; Trikojus; Journal of the Chemical Society; (1927); p. 1665 View in Reaxys
Br
Mg
O
O
Br O
O
Rx-ID: 40937699 View in Reaxys 21/27 Yield
Conditions & References in tetrahydrofuran, Time= 1h Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Li, Chunsheng; Wu, Wanqing; Jiang, Huanfeng; Chemical Communications; vol. 51; nb. 46; (2015); p. 9575 - 9578 View in Reaxys
O
camphor redoil O
Rx-ID: 5436204 View in Reaxys 22/27 Yield
Conditions & References Knoll,R.; View in Reaxys
O
sassafras oil O
Rx-ID: 5436205 View in Reaxys 23/27 Yield
Conditions & References Knoll,R.; View in Reaxys O
HO
Cl
N
O
O
O
O
zinc
O
O
Hg
(v2)
O
Rx-ID: 7977299 View in Reaxys 24/27 Yield
Conditions & References Paolini; Luzzi; Balbiano; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 273; Chemische Berichte; vol. 36; (1903); p. 3579 View in Reaxys Paolini; Luzzi; Balbiano; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 272; Chemische Berichte; vol. 36; (1903); p. 3579 View in Reaxys
Cl Al Cl
Cl
HO
E
O O
O
O
O
O
lithium alanate Rx-ID: 5706802 View in Reaxys 25/27
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Yield
Conditions & References Birch; Slaytor; Chemistry and Industry (London, United Kingdom); (1956); p. 1524 View in Reaxys
I
OH
I
O
O
potassium carbonate O
OH
Rx-ID: 7155062 View in Reaxys 26/27 Yield
Conditions & References Perkin; Trikojus; Journal of the Chemical Society; (1927); p. 1665 View in Reaxys
O O
Rx-ID: 5436203 View in Reaxys 27/27 Yield
Conditions & References Feugeas; Bulletin de la Societe Chimique de France; (1964); p. 1892 View in Reaxys Fujita; Yamashita; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3553 View in Reaxys
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