Diphenyl N-halosulfilimines : Preparation,decomposition, and reactions with nucleophiles |
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Authors: | Toshiaki Yoshimura Naomichi Furukawa Takeshi Akasaka Shigeru Oae |
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Affiliation: | Department of Applied Chemistry, Faculty of Engineering, Osaka City University ,Sugimoto-cho, Osaka, Japan;Department of Chemistry, The University of Tsukuba , Sakura-mura, Niihari-gun, Ibaraki, Japan |
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Abstract: | Diphenyl N chloro (l)-N bromo (2) and N-iodo-sulfilimines (3) were prepared by halogenation of diphenyl free sulfilimine. Compound 1 decomposed in benzene at room temperature. The decomposition of 1 is a chain reaction since the reaction was induced by chlorine or t-butyl hypochlorite affording diphenyl(diphenylsulfilimino) sulfonium chloride(4a) while it was inhibited by styrene or stilbene. Compound 4a was also obtained by the reaction of 1 with diphenyl sulfide in benzene. Decomposition of 1 in acetic acid proceeded smoothly affording various products. Compound 1 reacted with sulfides sulfoxides triarylphosphines and triethylamine affording the N-substituted iminosulfonium salts. Compounds 1 and 2 were hydrolyzed with sodium hydroxide affording diphenyl sulfoximine. The reaction of 1 with sodium cyanide gave diphenyl N cyanosulfilimine(17). The reaction of 1 with Grignard reagent gave diphenyl free sulfilimine. Compounds 2 and 3 are more stable than 1. Decomposition of 2 in benzene or acetic acid gave diphenyl(diphenylsulfilimino)sulfonium perbromide(4c) |
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