Sulphines. Part IV. Reactions of aromatic sulphines with diazoalkanes
作者:B. F. Bonini、G. Maccagnani、A. Wagenaar、L. Thijs、B. Zwanenburg
DOI:10.1039/p19720002490
日期:——
The cycloaddition reactions of aromatic sulphines, such as thiobenzophenone S-oxide and thiofluorenone S-oxide, with 2-diazopropane lead to 1,3,4-thiadiazoline 1-oxides in high yields. Diazomethane reacts more sluggishly with sulphines: only with thiofluorenone S-oxide was a cycloadduct obtained. The structure of the cycloadducts has been proven by photochemical extrustion of sulphur monoxide from
芳族硫,例如硫代二苯甲酮S-氧化物和硫代芴酮S-氧化物与2-重氮丙烷的环加成反应可高产率地生成1,3,4-噻二唑啉1-氧化物。重氮甲烷与硫的反应更慢:仅与硫代芴酮S-氧化物反应得到环加合物。环加合物的结构已通过光化学解离一氧化硫与2,2-二甲基-5,5-二-(对甲苯基)-1,3,4-噻二唑啉一氧化物的作用而得到证明。在溶液中,环加合物容易进行逆环加成。噻吨酮9-硫酮SSS的加合物'-三氧化物和2-重氮丙烷不仅还原成起始的硫,而且还显示出逆向的逆向加成反应,得到重氮噻吨黄酮SS-二氧化物和硫代丙酮S-氧化物。