Mechanistic Studies on the Generation and Properties of Superelectrophilic Singlet Carbenes from Bis(perfluoroalkanesulfonyl)bromonium Ylides
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- 作者：Kazunori Miyamoto ; Susumu Iwasaki ; Ryusuke Doi ; Taiga Ota ; Yufuko Kawano ; Junpei Yamashita ; Yuuta Sakai ; Norihiro Tada ; Masahito Ochiai ; Satoko Hayashi ; Waro Nakanishi ; Masanobu Uchiyama
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：April 15, 2016
- 年：2016
- 卷：81
- 期：8
- 页码：3188-3198
- 全文大小：590K
- 年卷期：0
- ISSN：1520-6904
文摘
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.