INTRAMOLECULAR TRAPPING OF THE NITRENE GENERATED BY PHOTOLYSIS OF S,S-DIPHENYL N-ACYLSULFILIMINE |
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| Authors: | Naomichi Furukawa Mitsuo Fukumura Takehiko Nishio Shigeru Oae |
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| Institution: | Department of Chemistry , University of Tsukuba , Sakura-mura, Niihari-gun, Ibaraki, 300-31 |
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| Abstract: | Abstract Various N-acyldiphenylsulfilimines (1a-k) were found to undergo photolysis in argon atmosphere, to afford the corresponding isocyanates, diphenyl sulfide and diphenyl disulfide. Attempts to trap intramolecularly the acylnitrene with olefinic linkage or sulfide afforded small amounts of the trapped products, whereas photolysis of N-mesitoyldiphenyl-sulfilimine (Ia) afforded a C–H inserted product of the nitrene in a substantial yield together with the isocyanate. Benzophenone-sensitized photolysis of Ia indicates that the nitrene generated is a singlet species. |
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