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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Volume 72, Issue 10


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

Vadim V. Bardin
  • Corresponding author
  • N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Lavrentiev Ave., 630090 Novosibirsk, Russia
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/ Alexander M. Maksimov
  • N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia
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Published Online: 2017-09-26 | DOI: https://doi.org/10.1515/znb-2017-0092


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.

Keywords: C-nucleophiles; organolithium; organomagnesium halides; pentafluorobenzenesulfonyl halides


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About the article

Received: 2017-05-29

Accepted: 2017-07-20

Published Online: 2017-09-26

Published in Print: 2017-09-26

Citation Information: Zeitschrift für Naturforschung B, Volume 72, Issue 10, Pages 731–737, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2017-0092.

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