Oxidation of 2-chloroethyl sulfides to sulfoxides by dimethyl sulfoxide

…, LL Szafraniec, WT Beaudry, YC Yang

文献索引：Hsu, Fu-Lian; Szafraniec, Linda L.; Beaudry, William T.; Yang, Yu-Chu Journal of Organic Chemistry, 1990 , vol. 55, # 13 p. 4153 - 4155

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被引用次数: 20

摘要

While most organic sulfides were not oxidized by dimethyl sulfoxide (DMSO), the alkyl 2- chloroethyl sulfides and bis (2-chloroethyl) sulfide slowly reacted with DMSO to produce the corresponding sulfoxides at 25-70 OC under nitrogen. The mechanism of the oxidation is proposed to involve nucleophilic substitution by DMSO followed by neighboring sulfur participation to form a transient sulfonium ion with a four-membered ring structure. The ...