Publication

Buttressing Effects on Haloarene Deprotonation: A Merely Kinetic or Also Thermodynamic Phenomenon?

Manfred Schlosser
2004
Journal Articles

Abstract

(2,6-Dichlorophenyl)- and (2,6-dibromophenyl)trialkylsilanes undergo hydrogen/metal interconversion preferentially at the 4- rather than 3-position. However, the organometallic species generated by such a "meta metalation" are thermodynamically less stable (i.e., more basic) than those that would result from an ordinary "ortho metalation". This was demonstrated by equilibration expts. based on permutational halogen/metal interconversion. A new buttressing effect can explain the unprecedented regioselectivity. It is supported by X-ray structures that reveal marked deformations of the benzene ring in halophenylsilanes. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/c42f094c-260d-4f74-aab6-e7011c5cb750

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Manfred Schlosser
2004
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/c42f094c-260d-4f74-aab6-e7011c5cb750

About this result

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