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Mechanism of the Grignard reaction

Mechanism of the Grignard reaction Mechanism of the Grignard reactions of aromatic ketones in THF was studied by spectroscopic and kinetic methods. The stable radical intermediates generated in the initial electron transfer from Grignard reagent to ketones are in a state of aggregated dimer of corresponding ion–radical pairs; in which two ketone anion radicals are bridged by a dimer di–cation of Grignard reagent. Subsequent alkyl radical transfer from dimeric Grignard reagent cation moiety to ketone anion radical aggregated each other are promoted by a participation of another neutral Grignard reagent. Proposed mechanism by present authors is able to explain well addition products/reduction products ratios in the Grignard reactions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Physical Organic Chemistry Wiley

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References (25)

Publisher
Wiley
Copyright
Copyright © 1989 Wiley Subscription Services, Inc., A Wiley Company
ISSN
0894-3230
eISSN
1099-1395
DOI
10.1002/poc.610020303
Publisher site
See Article on Publisher Site

Abstract

Mechanism of the Grignard reactions of aromatic ketones in THF was studied by spectroscopic and kinetic methods. The stable radical intermediates generated in the initial electron transfer from Grignard reagent to ketones are in a state of aggregated dimer of corresponding ion–radical pairs; in which two ketone anion radicals are bridged by a dimer di–cation of Grignard reagent. Subsequent alkyl radical transfer from dimeric Grignard reagent cation moiety to ketone anion radical aggregated each other are promoted by a participation of another neutral Grignard reagent. Proposed mechanism by present authors is able to explain well addition products/reduction products ratios in the Grignard reactions.

Journal

Journal of Physical Organic ChemistryWiley

Published: Apr 1, 1989

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