Nucleophilic Addition of Amines to Silyl- and Germyl-Substituted Thiophene 1,1-Dioxides
作者:Edmunds Lukevics、Pavel Arsenyan、Sergey Belyakov、Juris Popelis、Olga Pudova
DOI:10.1002/1099-0690(200009)2000:18<3139::aid-ejoc3139>3.0.co;2-q
日期:2000.9
Nucleophilic addition of secondary amines to tert-butyl-, trimethylsilyl- and trimethylgermyl-2,5-disubstituted thiophene 1,1-dioxides has been studied. It has been shown that the reactivity and reaction pathway depend strongly on the thiophene 1,1-dioxide structure, the basicity of the amine and the nature of the solvent. Addition of amines to 2,5bis(tert-butyl)thiophene 1,1-dioxide does not occur
已经研究了仲胺与叔丁基、三甲基甲硅烷基和三甲基锗基-2,5-二取代噻吩 1,1-二氧化物的亲核加成。已经表明,反应性和反应途径在很大程度上取决于噻吩 1,1-二氧化物结构、胺的碱性和溶剂的性质。胺与 2,5 双(叔丁基)噻吩 1,1-二氧化物的加成在有机或水性介质中均不会发生。在有机溶剂中,2,5-双(三甲基甲硅烷基)-、2-三甲基甲硅烷基-5-三甲基甲硅烷基-和 2,5-双(三甲基甲硅烷基)噻吩 1,1-二氧化物加一个哌啶分子,乙烯基硅烷片段比乙烯基锗烷之一。噻吩 1,1-二氧化物与吗啉和二乙胺的相应反应未能发生。在水里,添加吗啉和二乙胺(每种情况下一个分子)或二甲胺和哌啶(每种情况下两个分子)伴随着脱金属。3-piperidino-5-trimethylgermyl-2,3-dihydrothiophene 1,1-dioxide 的分子结构由 X 射线分析证实。