Mechanistic Studies on the Generation and Properties of Superelectrophilic Singlet Carbenes from Bis(perfluoroalkanesulfonyl)bromonium Ylides

Mechanistic Studies on the Generation and Properties of Superelectrophilic Singlet Carbenes from Bis(perfluoroalkanesulfonyl)bromonium Ylides

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(perfluoroalka...

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Veröffentlicht in:Journal of organic chemistry 2016-04, Vol.81 (8), p.3188-3198
Hauptverfasser: Miyamoto, Kazunori, Iwasaki, Susumu, Doi, Ryusuke, Ota, Taiga, Kawano, Yufuko, Yamashita, Junpei, Sakai, Yuuta, Tada, Norihiro, Ochiai, Masahito, Hayashi, Satoko, Nakanishi, Waro, Uchiyama, Masanobu
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00142