Cyclopentanecarboxylic acid [C6H10O2] by Asch

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73 reactions in Reaxys

2018-01-21 17h:51m:08s (EST)

73 reactions in Reaxys

2018-01-21 17h:51m:34s (EST)

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HO C

Rx-ID: 1999234 View in Reaxys 1/73 Yield 41.8 %

Conditions & References With dipotassium peroxodisulfate, BF4 (1-)*C24H51BCu3N3O16 (1+)*2H2O, water in acetonitrile, Time= 6h, T= 60 °C , p= 15201Torr , Autoclave Kirillov, Alexander M.; Karabach, Yauhen Y.; Kirillova, Marina V.; Haukka, Matti; Pombeiro, Armando J. L.; Dalton Transactions; vol. 40; nb. 24; (2011); p. 6378 - 6381 View in Reaxys

40 %

With dipotassium peroxodisulfate, C26H38Cu3N4O16, water in acetonitrile, Time= 6h, T= 60 °C , Autoclave, Green chemistry, Reagent/catalyst Ansari, Istikhar A.; Sama, Farasha; Raizada, Mukul; Shahid; Ahmad, Musheer; Siddiqi, Zafar A.; New Journal of Chemistry; vol. 40; nb. 11; (2016); p. 9840 - 9852 View in Reaxys

39.3 %

With dipotassium peroxodisulfate, [Cu2Mg2(μ-Htea)2(μ6-pma)(H2O)6]n*6nH2O, water in acetonitrile, Time= 4h, T= 60 °C , p= 15201Torr , Autoclave Kirillov, Alexander M.; Karabach, Yauhen Y.; Kirillova, Marina V.; Haukka, Matti; Pombeiro, Armando J. L.; Crystal Growth and Design; vol. 12; nb. 3; (2012); p. 1069 - 1074 View in Reaxys

26.7 %

Alkane hidrocarboxylation reactions General procedure: The alkane hydrocarboxylation experiments were performedfollowing a previously developed protocol [12]. In a typical experi-ment the reaction mixtures were prepared as follows: to 0.01 mmol of the compound 1 or 2 contained in a 20.0 mL stainless steel autoclave, equipped with a Teflon-coated magnetic stirring bar, were added 1.50 mmol of K2S2O8, 2.0 mL of H2O, 4.0 mL of MeCN (total solvent volume was 6.0 mL), and 1.00 mmol of alkane. Then the autoclave was closed and flushed with CO three times to removethe air, and finally pressurized with 20 atm of CO. CAUTION: Due tothe toxicity of CO, all operations should be carried out in a well-ventilated hood The reaction mixture was typically stirred for4 h at 60°C using a magnetic stirrer and an oil bath, whereupon it was cooled in an ice bath, degassed, opened and transferred to a flask. Diethyl ether (9.0 mL) and 45 L of cycloheptanone (typi-cal GC internal standard) were added. In the case of cycloheptanehydrocarboxylation, cyclohexanone (45 L) was used as a GC standard. The obtained mixture was vigorously stirred for 10 min, andthe organic layer was analyzed by gas chromatography (internalstandard method), revealing the formation of the corresponding monocarboxylic acids as major products Attribution of peaks was made by comparison with chromatograms of authentic samples With dipotassium peroxodisulfate, C36H50Cu2N4O4 (2+)*2NO3 (1-) in water, acetonitrile, Time= 4h, T= 60 °C , p= 15201Torr , Autoclave, Reagent/catalyst Fernandes, Tiago A.; André, Vânia; Kirillov, Alexander M.; Kirillova, Marina V.; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 357 - 367 View in Reaxys

19.2 %

With dipotassium peroxodisulfate, [Cu((2,3-dihydroxybenzylidene)-2-hydroxybenzohydrazide(-2H))]4*4EtOH, water in acetonitrile, Time= 4h, T= 60 °C , p= 15201Torr , Autoclave, Reagent/catalyst Sutradhar, Manas; Kirillova, Marina V.; Guedes Da Silva, M. Fatima C.; Liu, Cai-Ming; Pombeiro, Armando J. L.; Dalton Transactions; vol. 42; nb. 47; (2013); p. 16578 - 16587 View in Reaxys

0.105 mmol

With oxygen, copper in pyridine, acetic acid, p= 1520Torr , Ambient temperature Barton; Csuhai; Doller; Tetrahedron Letters; vol. 33; nb. 31; (1992); p. 4389 - 4392 View in Reaxys

20.5 - 22.2 12; 13 :In a typical experiment the reaction mixtures were prepared as follows. To a 13.0 mL stainless steel auto%Chromat. clave, equipped with a Teflon-coated magnetic stirring bar, were added 0-32.0 μmol (typically 8.0 μmol) of catalyst (optional), 1.00-2.00 mmol (typically 1.50 mtnol) <n="10"/>of K2S2O8, 2.0-3.0 mL of H2O, 2.0-4.0 mL of MeCN and

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1.00- 1.50 mmol (typically 1.00 mmol) of liquid alkane (in the case of pentane, cyclopentane, hexane and cyclohexane) . Then the autoclave was closed and flushed with dinitrogen three times for removing the air and pressurized with 20-40 atm (typically 20 atm) of carbon monoxide. In the case of using a gaseous alkane (ethane, propane or πbutane) , the reactor had been pressurized with 1-10 atm of this gas prior to the admission of CO. The reaction mixture was vigorously stirred for 2-6 h at 25-60 0C using a magnetic stirrer and an oil bath, whereupon it was cooled in an ice bath, degassed, opened and transferred to a Schlenk tube. Diethyl ether (9.0-11.0 mL) , to separate from the inorganic compounds, and cycloheptanone (90 μL, internal standard) were added. The obtained mixture was vigorously stirred and the organic layer was analyzed by gas chromatography (internal standard method) using a Fisons Instruments GC 8000 series gas chromatograph with a DB WAX fused silica capillary column (P/N 123-7032) and the Jasco-Borwin v.1.50 software. In some cases, the products were also identified by GC-MS, 1H and 13C-(1Hj NMR techniques, using a Trio 2000Fisons spectrometer with a coupled Carlo Erba(Auto/HRGC/MS) gas chromatograph, and a Varian UNITY 300NMR spectrometer, respectively. The catalysts have been obtained either according to the previously described methods t3a'4a'12] or from commercial sources.Examples of effects on the alkane carboxylation of various factors, such as the relative amounts of alkane, <n="11"/>carbon monoxide, oxidant, solvent and its composition, catalyst type and reaction temperature, are listed in Tables 1 and 2 and discussed below.2 - Examples; The carboxylation of alkanes typically proceeds more efficiently in the presence of a metal catalyst, thus leading to higher yields of carboxylic acids which can usually be achieved in a shorter reaction time and at lower reaction temperature, in comparison with the same reaction performed in the absence of catalyst.The tetracopper triethanolaminate complex [OeCu4(N(CH2CH2O)3J4(BOH)4] [BF4] 2 exhibits the highest level of activity among the tested catalysts (Table 2) . For this catalyst, the maximum overall yields for the various alkanes are in the following order: cyclohexanecarboxylic acid from cyclohexane {ca. 72percent, example 15) , 2- methylhexanoic and 2-ethylpentanoic acids from rzhexane(ca. 45percent, example 14), isobutyric and butyric acids from propane {ca. 38percent, example 9), 2-methylbutanoic acid from n- butane [ca. 30percent, example 10) , 2-meth.ylpentanoic and 2- ehtylbutanoic acids from npentane (ca.. 23percent, example 11) , cyclopentanecarboxylic acid from cyclopentane (ca. 22percent, example 12), and propionic acid from ethane (ca. 9percent, example 8) . The yields based on the peroxodisulphate oxidant are also high, being typically h, of those based on alkane; Other catalysts, namely [Cu2 (H2tea) 2{ C5H4 (COO) 2- l, 4}]n-2ωH2O, [Cu(H2tea) (N3)] , Cu (NO3) 2 .bul. 2.5H2O,Ca[V(ON(CH2COO)2J2] , K2Cr2O7, MnO2 and Fe (OH) 3 .bul. 0.5H2O, can also be applied for the carboxylation of e.g. cyclohexane <n="14"/>leading to yields of cyclohexanecarboxylic acid in the 14-39percent range (Table 2, examples 17-23) .The catalyst amount has only a slight effect on the product yield, but lower catalyst amounts lead to quite higher TONs. For example, in the case of cyclopentane carboxylation, a catalyst amount decrease from 8.0 to 2.0 μmol leads only to a slight yield lowering from 22.2 to20.5percent, whereas the TON increases from 42 to 153 (Table 2, examples 12 and 13) .In both metal-free and metal-catalysed processes the secondary carbon atom in alkanes is more easily carboxylated favouring the formation of branched carboxylic acids. Moreover, the partial oxidation of linear alkanes to carboxylic acids (typically occurring in TFA containing systems) or to alcohols and ketones does not proceed, to a considerable extent, in our processes.The efficiency of both metal-free and metal- catalysed processes for alkane carboxylation is dependent on various factors, namely the amount and composition of solvent mixture (the 1:1 or 1:2 H2O/MeCN volumetric ratio usually is very favourable but not an exclusive one) , and the CO pressure (the highest yields and selectivities are commonly achieved for the typical CO pressure of 20 atm) . Nevertheless, other factors such as the type and amount of catalyst, oxidant amount, relative amounts of all the reaction components and reaction time, also influence the obtained results. With dipotassium peroxodisulfate, water, [OCu4{N(CH2CH2O)3}4(BOH)4][BF4]2 in acetonitrile, Time= 6h, T= 50 °C , p= 15201 - 30402Torr , Product distribution / selectivity Patent; INSTITUTO SUPERIOR TECNICO; WO2008/88234; (2008); (A1) English View in Reaxys 22.2 With dipotassium peroxodisulfate, 2BF4 (1-)*C24H52B4Cu4N4O17 (2+), water in acetonitrile, Time= 6h, T= 50 °C , p= %Chromat. 22801.5Torr , Autoclave Kirillova, Marina V.; Kirillov, Alexander M.; Kuznetsov, Maxim L.; Silva, Jose A. L.; Frausto Da Silva, Joao J. R.; Pombeiro, Armando J. L.; Chemical Communications; nb. 17; (2009); p. 2353 - 2355 View in Reaxys 22.2 With dipotassium peroxodisulfate, 2BF4 (1-)*C24H53B4Cu4N4O17 (2+), water in acetonitrile, Time= 6h, T= 50 °C , p= %Chromat. 30402Torr , Autoclave Kirillova, Marina V.; Kirillov, Alexander M.; Pombeiro, Armando J. L.; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2936 - 2948 View in Reaxys

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21.4 With dipotassium peroxodisulfate, (OC2H4)(OHC2H4)NC2H4N(C2H4OH)Cu(thiocyanate) in water, acetonitrile, Time= %Chromat. 4h, T= 60 °C , p= 15201Torr , Autoclave Kirillov, Alexander M.; Kirillova, Marina V.; Shul'Pina, Lidia S.; Figiel, Pawel J.; Gruenwald, Katrin R.; Guedes Da Silva, M. Fatima C.; Haukka, Matti; Pombeiro, Armando J.L.; Shul'Pin, Georgiy B.; Journal of Molecular Catalysis A: Chemical; vol. 350; nb. 1-2; (2011); p. 26 - 34 View in Reaxys 24.6 With dipotassium peroxodisulfate, {[Cu2(pivalic acid)4(N-tert-butyldiethanolamine)](pivalic acid)}n, water in acetoni%Chromat. trile, Time= 4h, T= 60 °C , p= 15201Torr Nesterova, Oksana V.; Kirillova, Marina V.; Guedes Da Silva, M. Fatima C.; Boca, Roman; Pombeiro, Armando J. L.; CrystEngComm; vol. 16; nb. 5; (2014); p. 775 - 783 View in Reaxys 25.9 With potassium peroxodisulfate, Cu(1,10-phenanthroline)(1,2-ethanediphosphonic acid), water in acetonitrile, Time= %Chromat. 4h, T= 60 °C , p= 15201Torr , Autoclave, High pressure, Reagent/catalyst Demadis, Konstantinos D.; Anagnostou, Zafeiria; Panera, Aggeliki; Mezei, Gellert; Kirillova, Marina V.; Kirillov, Alexander M.; RSC Advances; vol. 7; nb. 29; (2017); p. 17788 - 17799 View in Reaxys HO O

Rx-ID: 3531221 View in Reaxys 2/73 Yield 81 %

Conditions & References Stage 1: With tetracarbonyldi-.mu.-chlorodirhodium(I), acetic acid, methyl iodide, Inert atmosphere, Schlenk technique Stage 2: With hydrogen, toluene-4-sulfonic acid, triphenylphosphine, Time= 16h, T= 20 - 180 °C , p= 52505.3Torr , Autoclave Ostapowicz, Thomas G.; Schmitz, Marc; Krystof, Monika; Klankermayer, Juergen; Leitner, Walter; Angewandte Chemie - International Edition; vol. 52; nb. 46; (2013); p. 12119 - 12123; Angew. Chem.; vol. 125; nb. 46; (2013); p. 12341 - 12345 View in Reaxys With hydrogenchloride, bis(1,5-cyclooctadiene)nickel (0), diethyl ether, (c-C6H11)2PCH2CH2-2-pyridyl, 1) THF, 20 deg C, 48 h, 2) -40 deg C to room temperature, 6 h, Yield given. Multistep reaction Hoberg; Ballesteros; Sigan; Jegat; Milchereit; Synthesis; nb. 5; (1991); p. 395 - 398 View in Reaxys

9.4 mg

With nickel(II) iodide, manganese, Bathocuproine, water in N,N-dimethyl-formamide, T= 50 °C , p= 760.051Torr , Schlenk technique Gaydou, Morgane; Moragas, Toni; Juliá-Hernández, Francisco; Martin, Ruben; Journal of the American Chemical Society; vol. 139; nb. 35; (2017); p. 12161 - 12164 View in Reaxys

Rx-ID: 13337635 View in Reaxys 3/73 Yield 96 %

Conditions & References 6 :Description 6: Cyclopentanecarboxylic acid; OHOHChromic anhydride (6 g, 0.06 mol) was added portionwise to water (21 ml) and theresulting solution cooled at 0°C. Concentrated sulphuric acid (6 ml) were added dropwiseand the solution stirred for 15 minutes. The resulting red solution was added dropwise to asolution of hydroxymethyl cyclopentane (2 g, 0.02 mol) in acetone (150 ml), keeping thetemperature Iower than 5°C.At the end of the addition the ice bath was removed and the reaction was stirred for 1h.Water (150 ml) and diethyl ether (200 ml) were added, the phases were separated andthe organic layer was extracted with 2M NaOH (3x120 ml). The aqueous phase was the-

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nacidified with 2M HCI to pH 2-3 and extracted with diethyl ether.The organic phase was dried with Na2SO4, filtered and evaporated to afford the crudeproduct, which was filtered through a silica pad to give the title product aes a colorless oil(2.2 g, 96percent yield).1HNMR (CDCI3) 5: 1.5-1.9 (8H, m), 2.75 (1H, m). Stage 1: With sulfuric acid, dichromic acid in water, acetone, Time= 1h, T= 0 - 5 °C Stage 2: With sodium hydroxide in diethyl ether, water Stage 3: With hydrogenchloride in water, pH= 2 - 3 Patent; GLAXO GROUP LIMITED; WO2006/2956; (2006); (A1) English View in Reaxys 79 %

With manganese(II) bromide, silver carbonate, potassium hydoxide in 1,3,5-trimethyl-benzene, Time= 20h, T= 50 165 °C , Schlenk technique, Inert atmosphere Ghalehshahi, Hajar Golshadi; Madsen, Robert; Chemistry - A European Journal; vol. 23; nb. 49; (2017); p. 11920 - 11926 View in Reaxys

65 %

With tert.-butylhydroperoxide, copper(l) chloride in decane, acetonitrile, T= 20 °C Mannam, Sreedevi; Sekar, Govindasamy; Synthetic Communications; vol. 40; nb. 19; (2010); p. 2822 - 2829 View in Reaxys

60 %

Stage 1: With [RuCl2(p-cymene)(iPr2-imy)], tricyclohexylphosphine tetrafluoroborate, potassium hydoxide in toluene, Time= 18h, Schlenk technique, Inert atmosphere, Reflux Stage 2: With hydrogenchloride in water, pH= 1 Santilli, Carola; Makarov, Ilya S.; Fristrup, Peter; Madsen, Robert; Journal of Organic Chemistry; vol. 81; nb. 20; (2016); p. 9931 - 9938 View in Reaxys Reaction Steps: 2 1: TEMPO; poly[4-(diacetoxyiodo)styrene] / acetone / 5 h / 20 °C 2: aq. TEMPO; poly[4-(diacetoxyiodo)styrene] / acetone / 24 h / 20 °C With poly[4-(diacetoxyiodo)styrene], 2,2,6,6-tetramethyl-piperidine-N-oxyl in acetone Tashino, Yousuke; Togo, Hideo; Synlett; nb. 11; (2004); p. 2010 - 2012 View in Reaxys O

HO HO

OH O

Rx-ID: 46956239 View in Reaxys 4/73 Yield 41 %, 26 %

Conditions & References With dihydrogen peroxide in tert-butyl alcohol, T= 50 °C , regioselective reaction Hu, Jiadong; Yu, Xin; Xie, Weiqing; Synlett; vol. 28; nb. 19; (2017); p. 2517 - 2524 View in Reaxys

Rx-ID: 9718205 View in Reaxys 5/73 Yield 95 %

Conditions & References With Co4HP2Mo15V3O62, N-(4-sulfonic acid)butyl triethylammonium tetrafluoroborate, dihydrogen peroxide in water, Time= 2h, T= 20 °C , Green chemistry Hu, Yu-Lin; Li, De-Jiang; Li, Dong-Sheng; RSC Advances; vol. 5; nb. 32; (2015); p. 24936 - 24943 View in Reaxys

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88 %

With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate, 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine in acetonitrile, T= 20 °C Zhao, Junfeng; Mueck-Lichtenfeld, Christian; Studer, Armido; Advanced Synthesis and Catalysis; vol. 355; nb. 6; (2013); p. 1098 - 1106 View in Reaxys With poly[4-(diacetoxyiodo)styrene], 2,2,6,6-tetramethyl-piperidine-N-oxyl in acetone, Time= 24h, T= 20 °C Tashino, Yousuke; Togo, Hideo; Synlett; nb. 11; (2004); p. 2010 - 2012 View in Reaxys HO

OH H

Rx-ID: 41410076 View in Reaxys 6/73 Yield

Conditions & References

70 %

With palladium diacetate, acetic anhydride, [(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate in toluene, Time= 24h, T= 70 °C , Inert atmosphere, Sealed tube, regioselective reaction Wang, Yang; Ren, Wenlong; Shi, Yian; Organic and Biomolecular Chemistry; vol. 13; nb. 31; (2015); p. 8416 8419 View in Reaxys HO

O O

Rx-ID: 39289226 View in Reaxys 7/73 Yield

Conditions & References

81 %

With 1,1'-bis-(diphenylphosphino)ferrocene, formic acid, palladium diacetate in toluene, Time= 24h, T= 90 °C , Inert atmosphere, regioselective reaction Wang, Yang; Ren, Wenlong; Li, Jingfu; Wang, Haining; Shi, Yian; Organic Letters; vol. 16; nb. 22; (2014); p. 5960 - 5963 View in Reaxys HO

Rx-ID: 7244143 View in Reaxys 8/73 Yield 62%

Conditions & References 29 : Example 29 Example 29 Into a 50 ml flask equipped with a magnetic stirrer and a reflux condenser, 570 mg of selenium dioxide, 2.6 g of Nmethylimidazole and 5.6 g of 42percent by weight aqueous tetrafluoroboric acid solution were charged and the resulting mixture was stirred at room temperature for 10 minutes to obtain a homogeneous solution containing a selenium-containing oxidation catalyst composition. To the homogeneous solution, 8.6 g of 30percent by weight aqueous hydrogen peroxide solution and 5 g of cyclohexanone were charged and the reaction was conducted at an inner temperature of 60°C for 1 hour. After competition of the reaction, 10 g of ethyl acetate was added to the reaction mixture to separate to an aqueous layer containing the selenium-containing oxidation catalyst composition and an ethyl acetate layer containing oxygen-containing compounds. The aqueous layer containing the selenium-containing oxidation catalyst composition was extracted twice with ethyl acetate to obtain an organic layer and an aqueous layer containing the selenium-containing oxidation catalyst composition. The organic layer obtained was mixed with the ethyl acetate layer obtained before to obtain an ethyl acetate layer containing cyclopentanecarboxylic acid.

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Yield: 62percent. Patent; Sumitomo Chemical Company, Limited; EP1797953; (2007); (A1) English View in Reaxys 56%

21 : EXAMPLE 21 EXAMPLE 21 Using a similar procedure to that described in Example 9 but starting with cyclopentanecarboxylic acid instead of 2phenylbutyric acid, methyl 4-(6-cyclopentancarboxamidoindol-1-ylmethyl)-3-methoxybenzoate was obtained as a solid in 56percent yield; partial NMR: 1.5-2.0 [br m, 8H, (CH2)4 ], 2.5-2.8 [br m, 1H, (CH2 4 CH], 7.2 (br s, 1H, NH). Patent; ICI Americas Inc.; US4997844; (1991); (A1) English View in Reaxys Herstellung von <1-14 C>Cyclopentancarbonsaeure Loftfield; ; (1958); p. 85 View in Reaxys Herstellung von Cyclopentan-<14 C>carbonsaeure Turner; Warne; Journal of the Chemical Society; (1953); p. 789,791, 793 View in Reaxys Regitz,M.; Rueter,J.; Chemische Berichte; vol. 102; (1969); p. 3877 - 3890 View in Reaxys Stork,G.; Borowitz,I.J.; Journal of the American Chemical Society; vol. 82; (1960); p. 4307 - 4315 View in Reaxys Lagercrantz,C. et al.; Acta Chemica Scandinavica (1947-1973); vol. 24; (1970); p. 550 - 560 View in Reaxys de Botton,M.; Bulletin de la Societe Chimique de France; (1975); p. 1773 - 1776 View in Reaxys White,D.R.; Wu,D.K.; Journal of the Chemical Society, Chemical Communications; (1974); p. 988 - 989 View in Reaxys Bailey,W.J.; Daly,J.J.; Journal of Organic Chemistry; vol. 29; (1964); p. 1249 - 1251 View in Reaxys Moriconi,E.J.; Dutta,C.P.; Journal of Organic Chemistry; vol. 35; (1970); p. 2443 - 2445 View in Reaxys Fusco,R. et al.; Gazzetta Chimica Italiana; vol. 91; (1961); p. 933 - 957 View in Reaxys Edwards; Lesage; Canadian Journal of Chemistry; vol. 41; (1963); p. 1592,1603; Journal of Organic Chemistry; vol. 24; (1959); p. 2071 View in Reaxys Chopard; Hudson; Journal of the Chemical Society [Section] B: Physical Organic; (1966); p. 1089,1093 View in Reaxys Peters; Journal of the Chemical Society; (1960); p. 1832,1836 View in Reaxys Kimura et al.; Journal of the Chemical Society, Chemical Communications; (1976); p. 787 View in Reaxys Olah; Welch; Journal of Organic Chemistry; vol. 43; (1978); p. 2830 View in Reaxys de Botton; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 272; (1971); p. 118 View in Reaxys Eidus; Pusizkii; Neftekhimiya; vol. 1; (1962); p. 82,59 View in Reaxys Cacace et al.; Annali di Chimica (Rome, Italy); vol. 50; (1960); p. 920,921-929 View in Reaxys Payne; Journal of Organic Chemistry; vol. 26; (1961); p. 4793,4796 View in Reaxys Goryaev et al.; Trudy Instituta Khimicheskikh Nauk, Akademiya Nauk Kazakhskoi SSR; vol. 19; (1967); p. 77,78-87; ; vol. 69; nb. 18646z; (1968) View in Reaxys

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Wiberg; Koch; Tetrahedron Letters; (1966); p. 1779 View in Reaxys Mc Killop et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 3381 View in Reaxys Patent; Upjohn; US4021478; (1977); ; vol. 87; nb. 39128 View in Reaxys Shatkina et al.; Doklady Chemistry; vol. 207; (1972); p. 977; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 207; (1972); p. 1144 View in Reaxys Reutov et al.; Doklady Chemistry; vol. 183; (1968); p. 1053; Doklady Akademii Nauk SSSR; vol. 183; (1968); p. 846 View in Reaxys Shatkina et al.; Doklady Chemistry; vol. 173; (1967); p. 224; Doklady Akademii Nauk SSSR; vol. 173; (1967); p. 113 View in Reaxys Shatkina et al.; Doklady Chemistry; vol. 219; (1974); p. 911; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 219; (1974); p. 1392 View in Reaxys Nakai et al.; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 2917,2918 View in Reaxys Winogradowa; Saw'jalow; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 4110,4076 View in Reaxys Wheeler et al.; Journal of Organic Chemistry; vol. 26; (1961); p. 2505 View in Reaxys Balaban; Nenitzescu; Tetrahedron; vol. 10; (1960); p. 55,62; ; p. 63 View in Reaxys Braidy; Bulletin de la Societe Chimique de France; (1967); p. 3489 View in Reaxys Paatz; Weisgerber; Chemische Berichte; vol. 100; (1967); p. 984 View in Reaxys Korobicyna et al.; Zhurnal Organicheskoi Khimii; vol. 4; (1968); p. 175,165 View in Reaxys Repetition of the procedure of Example 17 but using the carboxylic acids (as their sodium salts) enumerated below, the appropriate 25-substituted avermectins characterized in Table I were obtained: cyclohexane carboxylic acid cyclohex-3-ene carboxylic acid cyclopentane carboxylic acid 2-methylpent-3-enoic acid 2-methylpropionic acid ... Patent; Pfizer Inc.; US5089480; (1992); (A1) English View in Reaxys 42 : 3- (N-Cyclopentylmethyl-2(R)-pyrrolidinylmethyl)-5-(2-ethylsulphonylethyl)-1H-indole EXAMPLE 42 3- (N-Cyclopentylmethyl-2(R)-pyrrolidinylmethyl)-5-(2-ethylsulphonylethyl)-1H-indole Obtained as a foam by a procedure similar to that described in Example 18 (b), using Preparation 5 and cyclopentanecarboxylic acid. Rf 0.60 (SS 4). Found: C,67.74; H,8.55; N,6.81. C23 H34 N2 O2 S; 0.10 CH2 Cl2 requires C,67.59; H,8.36; N,6.79. δ(CDCl3): 1.10-1.95(14H,m), 2.08-2.22(1H,m), 2.30-2.42(2H,m), 2.70-2.98(6H,m), 3.16-3.50(6H,m), 5.30(0.20H,s), 7.02(1H,d), 7.10(1H,s), 7.32(1H,d), 7.42(1H,s), 8.35(1H,br s). Patent; Pfizer Inc.; US5639779; (1997); (A1) English View in Reaxys 7,7-dimethylbicyclo[2.2.1]heptan-2-yl; ... bicyclo[2.2.1]heptan-2-yl-3-methanol; cyclopentyl-2-carboxylic acid ethyl ester; cyclopentyl-2-carboxylic acid; 3-propionic acid ethyl ester; ...

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Patent; Elzein, Elfatih; Ibrahim, Prabha; Palle, Venkata; Varkhedkar, Vaibhav; Zablocki, Jeff; US2005/20532; (2005); (A1) English View in Reaxys 8.2 5 %Chromat. Patent; INSTITUTO SUPERIOR TECNICO; WO2008/88234; (2008); (A1) English View in Reaxys 7,7-dimethylbicyclo[2.2.1]heptan-2-yl; bicyclo[2.2.1]heptan-2-yl-3-carboxylic acid ethyl ester; bicyclo[2.2.1]heptan-2-yl-3-carboxylic acid bicyclo[2.2.1]heptan-2-yl-3-methanol; cyclopentyl-2-carboxylic acid ethyl ester; cyclopentyl-2-carboxylic acid; 3-propionic acid ethyl ester; 2-carboxycyclohexyl ethyl ester; 2-carboxybicyclo[2.2.1]hept-3-yl ethyl ester. Patent; Dhalla, Arvinder; Chisholm, Jeffrey; Belardinelli, Luiz; US2009/203689; (2009); (A1) English View in Reaxys

Cl O

O E

Rx-ID: 28826313 View in Reaxys 9/73 Yield

Conditions & References

12 %Spectr.

Stage 1: With titanium(IV) isopropylate in diethyl ether, T= 0 - 20 °C , Inert atmosphere Stage 2: With hydrogenchloride, water in diethyl ether, T= 0 °C , Inert atmosphere Stage 3: With hydrogenchloride, water in diethyl ether, T= 0 °C , Inert atmosphere, diastereoselective reaction Wolan, Andrzej; Cadoret, Frederic; Six, Yvan; Tetrahedron; vol. 65; nb. 36; (2009); p. 7429 - 7439 View in Reaxys HO C

Rx-ID: 29160077 View in Reaxys 10/73 Yield

Conditions & References

14.5 With dipotassium peroxodisulfate, 2BF4 (1-)*C24H53B4Cu4N4O17 (2+), water in acetonitrile, Time= 6h, T= 50 °C , p= %Chro15201Torr , Autoclave mat., 7 %Chromat. Kirillova, Marina V.; Kirillov, Alexander M.; Pombeiro, Armando J. L.; Advanced Synthesis and Catalysis; vol. 351; nb. 17; (2009); p. 2936 - 2948 View in Reaxys

O O

Rx-ID: 11220080 View in Reaxys 11/73 Yield

Conditions & References With water in phosphate buffer, pH= 7.2, Enzyme kinetics Cummins, Ian; Landrum, Marie; Steel, Patrick G.; Edwards, Robert; Phytochemistry; vol. 68; nb. 6; (2007); p. 811 - 818

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View in Reaxys

Cl O

racemate

Rx-ID: 9310122 View in Reaxys 12/73 Yield

Conditions & References

2.1 mmol, 90 %

Stage 1: With titanium(IV) isopropylate in diethyl ether, Time= 0.216667h, T= -78 - -50 °C Stage 2: in diethyl ether, Time= 0.5h, T= -78 - -30 °C Stage 3: With water-d2 in diethyl ether, Time= 2h, T= 20 °C Cadoret, Frederic; Retailleau, Pascal; Six, Yvan; Tetrahedron Letters; vol. 47; nb. 44; (2006); p. 7749 - 7753 View in Reaxys

54 %

Stage 1: With titanium(IV) isopropylate in diethyl ether, Time= 0.0833333h, T= -70 - -30 °C Stage 2: in diethyl ether, Time= 0.5h, T= -70 - -30 °C Stage 3: With water-d2 in diethyl ether, Time= 0.416667h, T= -30 - 20 °C Six, Yvan; European Journal of Organic Chemistry; nb. 7; (2003); p. 1157 - 1171 View in Reaxys O

Cl O

racemate

Rx-ID: 10505401 View in Reaxys 13/73 Yield

Conditions & References

88 %, Stage 1: With titanium(IV) isopropylate in diethyl ether, Time= 0.216667h, T= -78 - -50 °C 0.040 Stage 2: in diethyl ether, Time= 0.5h, T= -78 - -30 °C mmol, 0.13 Stage 3: With iodine in diethyl ether, Time= 2h, T= 20 °C mmol Cadoret, Frederic; Retailleau, Pascal; Six, Yvan; Tetrahedron Letters; vol. 47; nb. 44; (2006); p. 7749 - 7753 View in Reaxys F

F C

F O

Rx-ID: 5219818 View in Reaxys 14/73 Yield

Conditions & References With dipotassium peroxodisulfate, magnesium, Time= 30h, T= 80 °C , p= 38000Torr , Carboxylation Asadullah, Mohammad; Kitamura, Tsugio; Fujiwara, Yuzo; Chemistry Letters; nb. 6; (1999); p. 449 - 450 View in Reaxys With dipotassium peroxodisulfate, cobalt(II) acetate, Time= 30h, T= 70 °C , Carboxylation Asadullah, Mohammad; Taniguchi, Yuki; Kitamura, Tsugio; Fujiwara, Yuzo; Tetrahedron Letters; vol. 40; nb. 50; (1999); p. 8867 - 8871 View in Reaxys With dipotassium peroxodisulfate, Ca[V(HIDA)2], Time= 20h, T= 80 °C , p= 22800Torr , Product distribution, Further Variations: Pressures, Reagents Reis, Patricia M.; Silva, Jose A.L.; Palavra, Antonio F.; Frausto Da Silva, Joao J.R.; Pombeiro, Armando J.L.; Journal of Catalysis; vol. 235; nb. 2; (2005); p. 333 - 340 View in Reaxys

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OH O

Rx-ID: 9882569 View in Reaxys 15/73 Yield

Conditions & References With tert.-butylhydroperoxide, 2-methyl-1,3,2-benzothiaselenazole 1,1-dioxide in tert-butyl alcohol, Time= 15h, T= 65 °C , Product distribution, Further Variations: Reagents Potaczek; Giurg; Kloc; Maliszewska; Piasecki; Pietka; Mlochowski; Polish Journal of Chemistry; vol. 78; nb. 5; (2004); p. 687 - 697 View in Reaxys HO

BF3.2H2O Rx-ID: 24059274 View in Reaxys 16/73 Yield

Conditions & References 1 : Experiment 1 800 g of BF3.2H2O was charged to a one-liter stirred autoclave. The autoclave was pressurized with CO at 1250 psig, then heated to 55° C. The autoclave was maintained at these conditions, with continuous stirring, for one hour. 250 cc of a 50/50 (w/w) mixture of cyclopentene/cyclopentane was slowly added to the autoclave over a period of 2.75 hours. After adding the feed, the autoclave was kept for an additional three hours at same conditions. The autoclave was cooled to room temperature, vented, then drained into a vessel containing 340 g of water. Two distinct phases developed: an upper phase containing the reaction products and a lower phase containing the catalyst. GC analysis of the upper phase showed that the majority of the cyclopentene was converted to cyclopentanecarboxylic acid, in addition to some higher oligomers of the starting feed. The cyclopentane in the starting feed was largely intact. in Cyclopentane, water Patent; Saleh, Ramzi; US2002/177733; (2002); (A1) English View in Reaxys

Rx-ID: 8875880 View in Reaxys 17/73 Yield

Conditions & References With sodium perchlorate, water, T= 25 °C , Kinetics Andraos, John; Kresge, A. Jerry; Canadian Journal of Chemistry; vol. 78; nb. 4; (2000); p. 508 - 515 View in Reaxys O

Rx-ID: 555066 View in Reaxys 18/73 Yield 60 %

Conditions & References With poly(bisanthracenyl) diselenide, dihydrogen peroxide in tert-butyl alcohol, Time= 5h, Heating Giurg, Miroslaw; Mlochowski, Jacek; Synthetic Communications; vol. 29; nb. 13; (1999); p. 2281 - 2291 View in Reaxys

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45 %

With thallium(I) nitrate in acetic acid Cooper, Catherine N.; Jenner, Peter J.; Perry, Nigel B.; Russel-King, Jonquil; Storesund, Hans J.; Whiting, Mark C.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 605 - 612 View in Reaxys With selenium(IV) oxide, dihydrogen peroxide, tert-butyl alcohol Payne; Smith; Journal of Organic Chemistry; vol. 22; (1957); p. 1680 View in Reaxys

O HO

OH O

Rx-ID: 5149344 View in Reaxys 19/73 Yield

Conditions & References

60 %

With Bis(2-quinolinyl) diselenide in tert-butyl alcohol, Time= 3.5h, T= 65 °C , other reagents, reaction time, Product distribution Giurg, Miroslaw; Mlochowski, Jacek; Synthetic Communications; vol. 29; nb. 13; (1999); p. 2281 - 2291 View in Reaxys

N HO

Rx-ID: 4725602 View in Reaxys 20/73 Yield

Conditions & References With dirhodium tetraacetate in dichloromethane, Time= 5h, Yield given. Yields of byproduct given. Title compound not separated from byproducts Ceccherelli, Paolo; Curini, Massimo; Marcotullio, Maria Carla; Pisani, Emanuela; Rosati, Ornelio; Wenkert, Ernest; Tetrahedron; vol. 53; nb. 25; (1997); p. 8501 - 8506 View in Reaxys

HO O

Rx-ID: 4617743 View in Reaxys 21/73 Yield

Conditions & References

77 %

With titanium(IV) isopropylate, cyclohexylmagnesiumchloride in tetrahydrofuran, Ambient temperature Lee, Jinhwa; Cha, Jin Kun; Tetrahedron Letters; vol. 37; nb. 21; (1996); p. 3663 - 3666 View in Reaxys

Rx-ID: 1794271 View in Reaxys 22/73 Yield

Conditions & References With pyridine, bis(1,5-cyclooctadiene)nickel (0), sulfuric acid, 1) THF, a) -50 deg C, 1 h, b) room temperature, 14 h, 2) -40 deg C to room temperature, Yield given. Multistep reaction

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Hoberg; Ballesteros; Sigan; Jegat; Milchereit; Synthesis; nb. 5; (1991); p. 395 - 398 View in Reaxys HO O

Rx-ID: 3531218 View in Reaxys 23/73 Yield

Conditions & References With beryllium(II) chloride, hydrogenchloride, bis(1,5-cyclooctadiene)nickel (0), diethyl ether, (c-C6H11)2PCH2CH2-2pyridyl, 1) THF, 20 deg C, 48 h, 2) THF, room temperature, 12 h, 3) -40 deg C to room temperature, Yield given. Multistep reaction. Yields of byproduct given Hoberg; Ballesteros; Sigan; Jegat; Milchereit; Synthesis; nb. 5; (1991); p. 395 - 398 View in Reaxys HO

Rx-ID: 21064751 View in Reaxys 24/73 Yield

Conditions & References Reaction Steps: 2 1: 1) 2-<2-(dicyclohexylphosphino)ethyl>pyridine, bis(1,5-cyclooctadiene)nickel(0), 2) buta-1,3-diene, 3) 6 N Et2O/ HCl / 1) THF, 20 deg C, 48 h, 2) THF, 60 deg C, 24 h 2: 1) bis(1,5-cyclooctadiene)nickel(0), pyridine, 2) 2 N H2SO4 / 1) THF, a) -50 deg C, 1 h, b) room temperature, 14 h, 2) -40 deg C to room temperature With pyridine, hydrogenchloride, bis(1,5-cyclooctadiene)nickel (0), diethyl ether, (c-C6H11)2PCH2CH2-2-pyridyl, sulfuric acid, buta-1,3-diene Hoberg; Ballesteros; Sigan; Jegat; Milchereit; Synthesis; nb. 5; (1991); p. 395 - 398 View in Reaxys HO

O O

O S

Rx-ID: 3855532 View in Reaxys 25/73 Yield

Conditions & References

52 %, 23 %

With dipotassium peroxodisulfate, copper(I) sulfate in water, acetonitrile, Time= 4h, T= 80 °C , other alkenes, var. temp. and reaction time, Product distribution Perumal, P. Thirumalai; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1353 - 1356 View in Reaxys

52 %, 23 %

With dipotassium peroxodisulfate, copper(I) sulfate in water, acetonitrile, Time= 4h, T= 80 °C Perumal, P. Thirumalai; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1353 - 1356 View in Reaxys

Rx-ID: 24968245 View in Reaxys 26/73 Yield

Conditions & References 2.A : 5'-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one A solution of 46.08 g of cyclopentanecarboxylic acid chloride in 200 ml of anhydrous ether was added to a 0° C. solution of 68.4 ml of phenylhydrazine in 200 ml of anhydrous ether over a 1 hour period. The reaction was stirred an additional 1 hour and diluted with water.

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The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed sequentially with 1N hydrochloric acid, water, a saturated sodium bicarbonate solution, water, and a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. Recrystallization of the residue from ethyl acetate/hexane provided 55.9 g of the desired subtitle intermediate as a white powder, m.p. 138°-139° C. With phenylhydrazine in hexane, ethyl acetate Patent; Eli Lilly and Company; US4617302; (1986); (A1) English View in Reaxys HO H 2N

Rx-ID: 25122353 View in Reaxys 27/73 Yield

Conditions & References 12 : EXAMPLE 12 The cyclopentanecarboxylic acid (m.p. 278°-280° C. after crystallisation from methanol) used as starting material was obtained by a similar process to that described in the second part of Example 11, except that 1-aminocyclopentanecarboxylic acid was used as starting material in place of L-valine. Patent; Imperial Chemical Industries PLC; US4399138; (1983); (A1) English View in Reaxys

Cl C

O O O

Na +

O–

Rx-ID: 2002231 View in Reaxys 28/73 Yield

Conditions & References With iron(III) chloride, sodium hydride in 1,2-dimethoxyethane, Time= 30h, T= 65 °C , C5H9Cl/FeCl3=10, C5H9Cl/NaH/Am-t-ONa/FeCl3=10/40/20/1 mmol, Product distribution Brunet, Jean-Jacques; Sidot, Christian; Caubere, Paul; Journal of Organic Chemistry; vol. 46; nb. 15; (1981); p. 3147 - 3149 View in Reaxys

O HO

O O

OH O

Rx-ID: 2343420 View in Reaxys 29/73 Yield

Conditions & References With manganese(IV) oxide, perchloric acid, tris(2,2’-bipyridine)ruthenium(II), Time= 0.333333h, in prsence and absence of air; ΔH(act.), ΔG(act.), ΔS(act.), Product distribution, Thermodynamic data, Rate constant Audsley, Adrian J.; Quick, Geoffrey R.; Littler, John S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 557 - 560 View in Reaxys

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Rx-ID: 2567925 View in Reaxys 30/73 Yield

Conditions & References

56 %, 5 %

With sodium hydroxide, Time= 24h, Ambient temperature Sakai, Takashi; Amano, Eiichiro; Kawabata, Akifumi; Takeda, Akira; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 43 - 47 View in Reaxys

O HO O

O O

Rx-ID: 2572005 View in Reaxys 31/73 Yield

Conditions & References

5 %, 55 %

With sodium hydroxide Sakai, Takashi; Amano, Eiichiro; Kawabata, Akifumi; Takeda, Akira; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 43 - 47 View in Reaxys

H 2N

Rx-ID: 538318 View in Reaxys 32/73 Yield

Conditions & References With perchloric acid, sodium nitrite Edwards; Lesage; Canadian Journal of Chemistry; vol. 41; (1963); p. 1592,1603; Journal of Organic Chemistry; vol. 24; (1959); p. 2071 View in Reaxys Edwards; Lesage; Journal of Organic Chemistry; vol. 24; (1959); p. 2071 View in Reaxys O

Cl –O

Na +

Rx-ID: 794883 View in Reaxys 33/73 Yield

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Mousseron; Jacquier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 374; Bulletin de la Societe Chimique de France; (1950); p. 698,702 View in Reaxys O

O– Na +

Rx-ID: 794887 View in Reaxys 34/73 Yield

Conditions & References Stork,G.; Borowitz,I.J.; Journal of the American Chemical Society; vol. 82; (1960); p. 4307 - 4315 View in Reaxys Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys Tokura; Oda; Rikagaku Kenkyusho Iho; vol. 22; (1943); p. 840; ; (1949); p. 2176 View in Reaxys Jackman; Bergman; Archer; Journal of the American Chemical Society; vol. 70; (1948); p. 497,499 View in Reaxys Loftfield; Journal of the American Chemical Society; vol. 72; (1950); p. 632 View in Reaxys Mousseron; Jacquier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 374; Bulletin de la Societe Chimique de France; (1950); p. 698,702 View in Reaxys With ethanol, Eindampfen der Reaktionsloesung und anschliessend Versetzen mit Wasser Tokura; Oda; Rikagaku Kenkyusho Iho; vol. 22; (1943); p. 840; ; (1949); p. 2176 View in Reaxys Jackman; Bergman; Archer; Journal of the American Chemical Society; vol. 70; (1948); p. 497,499 View in Reaxys HO

OH HO

(8ac)-octahydro-naphthalene-4ar-carboxylic acid

S OO

Rx-ID: 6182342 View in Reaxys 35/73 Yield

Conditions & References Koch; Haaf; Justus Liebigs Annalen der Chemie; vol. 618; (1958); p. 251,261 View in Reaxys

OH HO

(8ac)-octahydro-naphthalene-4ar-carboxylic acid

S OO

Rx-ID: 7065677 View in Reaxys 36/73 Yield

Conditions & References Koch; Haaf; Justus Liebigs Annalen der Chemie; vol. 618; (1958); p. 251,261 View in Reaxys O Cl

–O

Na +

Rx-ID: 794880 View in Reaxys 37/73 Yield

Conditions & References With methanol Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys Stevens; Tazuma; Journal of the American Chemical Society; vol. 76; (1954); p. 715

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View in Reaxys Mousseron; Jacquier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 374; Bulletin de la Societe Chimique de France; (1950); p. 698,702 View in Reaxys O –

Na +

Rx-ID: 794881 View in Reaxys 38/73 Yield

Conditions & References Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys O O–

Na +

Rx-ID: 794886 View in Reaxys 39/73 Yield

Conditions & References With ethanol Mousseron; Jacquier; Bulletin de la Societe Chimique de France; (1950); p. 698,705 View in Reaxys Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys

Rx-ID: 794939 View in Reaxys 40/73 Yield

Conditions & References With methanol, potassium hydroxide Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys

sodium

Rx-ID: 5714566 View in Reaxys 41/73 Yield

Conditions & References Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys HO O

sodium

O HO

Rx-ID: 5714567 View in Reaxys 42/73 Yield

Conditions & References Mousseron et al.; Bulletin de la Societe Chimique de France; (1952); p. 767,775 View in Reaxys

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HO O

O– Na +

Rx-ID: 23409 View in Reaxys 43/73 Yield

Conditions & References anschliessend Behandeln mit Wasser Mousseron; Jacquier; Bulletin de la Societe Chimique de France; (1950); p. 698,705 View in Reaxys HO

O Cl

Rx-ID: 23410 View in Reaxys 44/73 Yield

Conditions & References With sodium ethanolate, anschliessendes Behandeln mit H2O Mousseron; Jacquier; Bulletin de la Societe Chimique de France; (1950); p. 698,705 View in Reaxys HO

Rx-ID: 285588 View in Reaxys 45/73 Yield

Conditions & References With potassium permanganate Plate et al.; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 472,475; engl. Ausg. S. 505, 508 View in Reaxys HO

C O Rx-ID: 7244144 View in Reaxys 46/73 Yield

Conditions & References With hydrogenchloride, Ni(CO4)4, nickel dichloride, T= 275 °C , p= 36775.4Torr Adkins; Rosenthal; Journal of the American Chemical Society; vol. 72; (1950); p. 4550 View in Reaxys HO

Rx-ID: 22334921 View in Reaxys 47/73 Yield

Conditions & References Reaction Steps: 2 1: chloroform 2: ethanolic sodium ethylate / anschliessendes Behandeln mit H2O With chloroform, sodium ethanolate Mousseron; Jacquier; Bulletin de la Societe Chimique de France; (1950); p. 698,705 View in Reaxys

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O O–

Na +

Rx-ID: 794885 View in Reaxys 48/73 Yield

Conditions & References Mousseron; Jacquier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 374; Bulletin de la Societe Chimique de France; (1950); p. 698,702 View in Reaxys HO

OH H 2N 2

etheric cyclopentyl magnesium bromide Rx-ID: 7244145 View in Reaxys 49/73

Yield

Conditions & References Hey; Musgrave; Journal of the Chemical Society; (1949); p. 3156,3160 View in Reaxys Neunhoeffer; Schlueter; Justus Liebigs Annalen der Chemie; vol. 526; (1936); p. 65,70 View in Reaxys Kohlrausch; Skrabal; Monatshefte fuer Chemie; vol. 70; (1937); p. 44,52 View in Reaxys HO

Rx-ID: 286086 View in Reaxys 50/73 Yield

Conditions & References Oxydation und anschliessende Hydrierung Tiffeneau; Tchoubar; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 212; (1941); p. 581,585 View in Reaxys

Rx-ID: 315613 View in Reaxys 51/73 Yield

Conditions & References durch Oxydation und anschliessende Hydrierung Tiffeneau; Tchoubar; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 212; (1941); p. 581,585 View in Reaxys O

-2 (v1)

HO HO

(v1)

aqueous KOH

2-hydroxy-cyclohexanone-(1) Rx-ID: 7998944 View in Reaxys 52/73

Yield

Conditions & References Wenuss-Danilowa; Zhurnal Obshchei Khimii; vol. 6; (1936); p. 1784,1793; Chem. Zentralbl.; vol. 108; nb. I; (1937); p. 4088

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View in Reaxys HO

Rx-ID: 266485 View in Reaxys 53/73 Yield

Conditions & References With sodium hypobromide Nenitzescu; Cantuniari; Chemische Berichte; vol. 65; (1932); p. 807,811 View in Reaxys HO

Rx-ID: 22079320 View in Reaxys 54/73 Yield

Conditions & References Reaction Steps: 2 1: AlCl3 / 0 °C 2: aqueous sodium hypobromite solution With aluminium trichloride, sodium hypobromide Nenitzescu; Cantuniari; Chemische Berichte; vol. 65; (1932); p. 807,811 View in Reaxys

Rx-ID: 143654 View in Reaxys 55/73 Yield

Conditions & References With nickel, T= 170 - 175 °C , Hydrogenation Eykman; Chem. Zentralbl.; vol. 82; nb. II; (1911); p. 1029 View in Reaxys With methanol, Pt/Al2O3, colloid, Hydrogenation Skraup; Binder; Chemische Berichte; vol. 62; (1929); p. 1135 View in Reaxys

colloid/al palladium

Rx-ID: 6676326 View in Reaxys 56/73 Yield

Conditions & References T= 20 °C , Hydrogenation Skraup; Binder; Chemische Berichte; vol. 62; (1929); p. 1135 View in Reaxys

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cyclopentyl-<2-oxy-phenyl>-ketone

Rx-ID: 8273600 View in Reaxys 57/73 Yield

Conditions & References T= 340 °C , im Rohr Skraup; Binder; Chemische Berichte; vol. 62; (1929); p. 1135 View in Reaxys Br

OH H 2N 2

Rx-ID: 849559 View in Reaxys 58/73 Yield

Conditions & References With diethyl ether Talbot; Adams; Journal of the American Chemical Society; vol. 49; (1927); p. 2041 View in Reaxys O

Rx-ID: 794943 View in Reaxys 59/73 Yield

Conditions & References With potassium hydroxide Faworski; Boshowski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 1100; Chem. Zentralbl.; vol. 86; nb. I; (1915); p. 984 View in Reaxys O

alcoholic KOH-solution

Rx-ID: 5809526 View in Reaxys 60/73 Yield

Conditions & References Faworski; Boshowski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 1100; Chem. Zentralbl.; vol. 86; nb. I; (1915); p. 984 View in Reaxys

Ag2O Rx-ID: 7047083 View in Reaxys 61/73 Yield

Conditions & References Tiffeneau; View in Reaxys Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 159; (1914); p. 772; View in Reaxys

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nickel Rx-ID: 6676297 View in Reaxys 62/73 Yield

Conditions & References T= 170 - 175 °C , Hydrogenation Eykman; ; vol. 8; p. 658; Chem. Zentralbl.; vol. 82; nb. II; (1911); p. 1029 View in Reaxys

Rx-ID: 276678 View in Reaxys 63/73 Yield

Conditions & References With carbon dioxide, magnesium Zelinsky; Chemische Berichte; vol. 41; (1908); p. 2629 View in Reaxys

Rx-ID: 22125070 View in Reaxys 64/73 Yield

Conditions & References Reaction Steps: 2 1: hydrochloric acid / 110 °C 2: magnesium; CO2 With hydrogenchloride, carbon dioxide, magnesium Zelinsky; Chemische Berichte; vol. 41; (1908); p. 2629 View in Reaxys

Rx-ID: 706060 View in Reaxys 65/73 Yield

Conditions & References Reaktion ueber mehrere Stufen Wislicenus; Gaertner; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 333 View in Reaxys Rupe; Lotz; Justus Liebigs Annalen der Chemie; vol. 327; (1903); p. 184 View in Reaxys Reaction Steps: 2 1: diethyl ether; fuming hydrochloric acid 2: Reaktion ueber mehrere Stufen With hydrogenchloride, diethyl ether Wislicenus; Gaertner; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 333 View in Reaxys

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O O

Rx-ID: 271069 View in Reaxys 66/73 Yield

Conditions & References beim Destillieren Haworth; Perkin; Journal of the Chemical Society; vol. 65; (1894); p. 104; Chemische Berichte; vol. 26; (1893); p. 2249 View in Reaxys

Rx-ID: 64315 View in Reaxys 67/73 Yield

Conditions & References With hydrogenchloride Wislicenus; Gaertner; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 333 View in Reaxys

HO HO

Rx-ID: 120749 View in Reaxys 68/73 Yield

Conditions & References Reaktion ueber mehrere Stufen Wislicenus; Gaertner; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 333 View in Reaxys HO

Rx-ID: 22035957 View in Reaxys 69/73 Yield

Conditions & References Reaction Steps: 2 1: alcohol / 200 °C 2: hydrochloric acid With hydrogenchloride, ethanol Wislicenus; Gaertner; Justus Liebigs Annalen der Chemie; vol. 275; (1893); p. 333 View in Reaxys O

Cl –O

1.1-diethoxy-cyclohexanol-(2)

Na +

Rx-ID: 5809527 View in Reaxys 70/73 Yield

Conditions & References Stevens; Tazuma; Journal of the American Chemical Society; vol. 76; p. 1954> 715, 717 View in Reaxys

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O O–

Na +

1.1-diethoxy-cyclohexanol-(2) Rx-ID: 5809528 View in Reaxys 71/73

Yield

Conditions & References Stevens; Tazuma; Journal of the American Chemical Society; vol. 76; p. 1954> 715, 717 View in Reaxys O

Cl –

1.1-dimethoxy-cyclohexanol-(2)

Rx-ID: 5809529 View in Reaxys 72/73 Yield

Conditions & References Stevens; Tazuma; Journal of the American Chemical Society; vol. 76; p. 1954> 715, 717 View in Reaxys O O– Na +

1.1-dimethoxy-cyclohexanol-(2) Rx-ID: 5809530 View in Reaxys 73/73

Yield

Conditions & References Stevens; Tazuma; Journal of the American Chemical Society; vol. 76; p. 1954> 715, 717 View in Reaxys

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