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Competition between π-arene and lone-pair halogen coordination of silylium ions?


Romanato, P; Duttwyler, S; Linden, A; Baldridge, K K; Siegel, J S (2011). Competition between π-arene and lone-pair halogen coordination of silylium ions? Journal of the American Chemical Society, 133(31):11844-11846.

Abstract

n 2,6-diarylphenylSiR(2) cations, the 2,6-diarylphenyl (m-terphenyl) scaffold blocks incoming nucleophiles and stabilizes the positive charge at silicon by lateral ring interactions. Direct ortho-halogen and π-electron-rich face coordination to silicon has been seen. For a series of cations bearing 2,6-difluoro-2',6'-dimethyl-X(n)-substituted rings, the relative contribution of these two modes of stabilization has been assessed. Direct coordination from an aryl fluoride is found to be comparable to that from the mesityl π-face.

© 2011 American Chemical Society

Abstract

n 2,6-diarylphenylSiR(2) cations, the 2,6-diarylphenyl (m-terphenyl) scaffold blocks incoming nucleophiles and stabilizes the positive charge at silicon by lateral ring interactions. Direct ortho-halogen and π-electron-rich face coordination to silicon has been seen. For a series of cations bearing 2,6-difluoro-2',6'-dimethyl-X(n)-substituted rings, the relative contribution of these two modes of stabilization has been assessed. Direct coordination from an aryl fluoride is found to be comparable to that from the mesityl π-face.

© 2011 American Chemical Society

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2011
Deposited On:08 Jan 2012 17:59
Last Modified:05 Apr 2016 15:18
Publisher:American Chemical Society
ISSN:0002-7863
Publisher DOI:https://doi.org/10.1021/ja2040392
PubMed ID:21766853

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