Perfluoro tertiary alcohols. III. (Perfluoroalkyl)- and (perfluorooxaalkyl)-trimethylsilanes in the synthesis of perfluorinated tertiary alcohols☆

作者: Grace J. Chen , Loomis S. Chen , Kalathil C. Eapen , Wayne E. Ward

DOI: 10.1016/0022-1139(94)03068-5

关键词: Yield (chemistry)Tertiary alcoholsMedicinal chemistryAlcoholKetoneTrifluoromethylOrganic chemistryChemistry

摘要: Abstract High-molecular weight perfluorinated tertiary alcohols, R f 1 2 3 C(OH) = n-C 8 F 17 , =CF =n-C 6 13 ; (CF ) CFO(CF 4 CF ,·R C 7 O[CF(CF )CF O] CF(CF ), O[CF )O] ( IIIa–d have been prepared by the reactions of (perfluoroalkyl)- and (perfluorooxaalkyl)-trimethylsilanes Ia–d with fluoroketones IIa–c ). Ketones containing a trifluoromethyl group as well higher molecular substituents studied under different experimental conditions. The yield alcohol is influenced solvents, reaction temperatures, type concentration metal fluorides, structures fluoroalkyltrimethylsilanes fluoroketones. has extended to carbonyl compounds other than ketones. While secondary acid fluoride gave good ketone, no was observed esters.

参考文章(9)
Loomis S. Chen, Grace J. Chen, Reaction of phosphorus pentachloride with perhalo carbonyl-containing compounds Journal of Fluorine Chemistry. ,vol. 42, pp. 371- 387 ,(1989) , 10.1016/S0022-1139(00)83930-5
Charles F. Smith, Edward J. Soloski, Christ Tamborski, Synthesis and reactions of perfluoro-n-octylmagnesium bromide Journal of Fluorine Chemistry. ,vol. 4, pp. 35- 45 ,(1974) , 10.1016/S0022-1139(00)81720-0
Ingo Ruppert, Klaus Schlich, Wolfgang Volbach, Die ersten CF3-substituierten organyl(chlor)silane Tetrahedron Letters. ,vol. 25, pp. 2195- 2198 ,(1984) , 10.1016/S0040-4039(01)80208-2
Ramesh Krishnamurti, Donald R. Bellew, G. K. Surya Prakash, Preparation of trifluoromethyl and other perfluoroalkyl compounds with (perfluoroalkyl)trimethylsilanes Journal of Organic Chemistry. ,vol. 56, pp. 984- 989 ,(1991) , 10.1021/JO00003A017
Stefan P. Kotun, John D. O. Anderson, Darryl D. Des Marteau, Fluorinated tertiary alcohols and alkoxides from nucleophilic trifluoromethylation of carbonyl compounds Journal of Organic Chemistry. ,vol. 57, pp. 1124- 1131 ,(1992) , 10.1021/JO00030A018