Synthesis of Polyfluorinated Tertiary Alcohols Using Ring Opening Reactions of 2,2-Bis(trifluoromethyl)oxirane
作者:Viacheslav A. Petrov
DOI:10.1055/s-2002-34857
日期:——
This paper describes new reactions of 2,2-bis(trifluoro)-methyl)oxirane (1). Ring opening of 1 by oxygen, nitrogen, sulfur or carbon nucleophiles (Nu ) proceeds regioselectively, with exclusive formation of tertiary alcohols: NuCH 2 C(CF 3 ) 2 OH. The reaction of 1 with strong acids (HX) is also regioselective and proceeds under mild conditions leading to the formation of XCH 2 C(CF 3 ) 2 OH (X = FSO
本文介绍了 2,2-双(三氟)-甲基)环氧乙烷 (1) 的新反应。氧、氮、硫或碳亲核试剂 (Nu ) 对 1 的开环以区域选择性方式进行,仅形成叔醇:NuCH 2 C(CF 3 ) 2 OH。1 与强酸 (HX) 的反应也是区域选择性的,并且在温和条件下进行,导致形成 XCH 2 C(CF 3 ) 2 OH (X = FSO 2 O, CF 3 SO 2 O, Cl, 1)。然而,向 1 中加入乙酸需要升高的温度和 TaF 5 催化剂。1 与亲核或亲电试剂的高选择性反应为含有 CH 2 C(CF 3 ) 2 OH 基团的材料提供了一种简单而通用的途径。