Synthesis and Amine-Induced Ring-Opening of Silyl-Substituted Thiophene 1,1-Dioxides
作者:S. Gronowitz、A. -B. Hörnfeldt、E. Lukevics、O. Pudova
DOI:10.1055/s-1994-25401
日期:——
Amine-induced ring-opening of the silylated thiophene 1,1-dioxides was used for the preparation of silyl-substituted dienes. Thus, the reaction of 2,5-dimethyl-3-trimethylsilylthiophene 1,1-dioxide (5) with piperidine at 100°C led to 3-trimethylsilyl-6-(1-piperidino)-(2Z,4E)-2,4-hexadiene (8) and the piperidine-induced ring-opening of 2-methyl-5-dimethylbutylsilylthiophene 1,1-dioxide gave 1-dimethylbutylsilyl-5-(1-piperidino)-(1E,3E)-1,3-pentadiene (9) as the main product.
甲硅烷基化噻吩 1,1-二氧化物的胺诱导开环用于制备甲硅烷基取代的二烯。因此,2,5-二甲基-3-三甲基甲硅烷基噻吩1,1-二氧化物(5)与哌啶在100℃下反应生成3-三甲基甲硅烷基-6-(1-哌啶基)-(2Z,4E)-2, 4-己二烯(8)和哌啶诱导的2-甲基-5-二甲基丁基甲硅烷基噻吩1,1-二氧化物的开环得到1-二甲基丁基甲硅烷基-5-(1-哌啶基)-(1E,3E)-1,3-主要产品为戊二烯(9)。