Mechanistic Studies on the Generation and Properties of Super-electrophilic Singlet Carbenes from Bis(perfluoroalkanesulfonyl)bromonium Ylides.

Kazunori Miyamoto,Susumu Iwasaki,Ryusuke Doi,Taiga Ota,Yufuko Kawano, Junpei Yamashita,Yuuta Sakai,Norihiro Tada,Masahito Ochiai,Satoko Hayashi,Waro Nakanishi,Masanobu Uchiyama

JOURNAL OF ORGANIC CHEMISTRY（2016）

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摘要

Pyrolysis of bis(perfluoroalkanesulfonyl)bromonium ylides in various olefins results in highly stereospecific formation of cyclopropanes via unimolecular decomposition. Product analysis, kinetic study, substituent effects, and theoretical study revealed the generation of singlet bis(perfluoroalkanesulfonyl)carbenes stabilized by intramolecular coordination of sulfonyl oxygen.

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关键词

superelectrophilic singlet carbenes

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