Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides-Reference-Cited by-同舟云学术

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

Published:2017-09-26 Issue:10 Volume:72 Page:731-737
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Bardin Vadim V.¹,Maksimov Alexander M.²

Affiliation:

1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry , Siberian Branch, Russian Academy of Sciences , 9 Lavrentiev Ave. , 630090 Novosibirsk , Russia

2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry , Siberian Branch, Russian Academy of Sciences , 630090 Novosibirsk , Russia

Abstract

Abstract C6F5SO2Cl reacts with organolithiums and organomagnesium halides RM (R=Me, Bu, Ph; M=Li, MgX) to give mainly C6F5H and C6F5Cl. C6F5SO2Br and PhMgBr form C6F5H and (C6F5S)2. This is in contrast to known transformations of them which yield exclusively C6F5SO2Nu under the action of O- and N-nucleophiles. Alternatively, C6F5SO2F is converted to C6F5SO2R and 4-BuC6F4SO2F or 2-PhC6F4SO2Ph under the same conditions. When R=Me, minor amounts of (C6F5SO2)2CH2 and 4-C6F5SO2CH2C6F4SO2F form in addition to C6F5SO2CH3.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2017-0092/pdf

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