Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides

Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides Full article

Journal

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
ISSN: 0932-0776

Output data

Year: 2017, Volume: 72, Number: 10, Pages: 731-737 Pages count : 7 DOI: 10.1515/znb-2017-0092

Tags

C-nucleophiles; organolithium; organomagnesium halides; pentafluorobenzenesulfonyl halides

Authors

Bardin Vadim V. ¹ , Maksimov Alexander M. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Lavrentiev Ave, Novosibirsk 630090, Russia

C6F5SO2 Cl reacts with organolithiums and organomagnesium halides RM (R = Me, Bu, Ph; M = Li, MgX) to give mainly C6F5H and C6F5Cl. C6F5SO2 Br and PhMgBr form C6F5H and (C6F5S)(2). This is in contrast to known transformations of them which yield exclusively C6F5SO2 Nu under the action of O- and N-nucleophiles. Alternatively, C6F5SO2F is converted to C6F5SO2 R and 4-BuC6F4SO2F or 2-PhC6F4SO2Ph under the same conditions. When R = Me, minor amounts of (C6F5SO2)(2) CH2 and 4-C6F5SO2CH2C6F4SO2F form in addition to C6F5SO2CH3.

Bardin V.V. , Maksimov A.M.
Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences. 2017. V.72. N10. P.731-737. DOI: 10.1515/znb-2017-0092 WOS Scopus РИНЦ

Published print:	Sep 26, 2017
Published online:	Sep 26, 2017

Web of science	WOS:000414612700006
Scopus	2-s2.0-85030845269
Elibrary	31094454
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