Journal of organometallic chemistry

Mechanistic studies on the reactions of trimethylsilanide and trimethylstannylide ions with haloarenes in hexamethylphosphoramide

A Postigo, SE Vaillard, RA Rossi

Index: Postigo, Al; Vaillard, Santiago E.; Rossi, Roberto A. Journal of Organometallic Chemistry, 2002 , vol. 656, # 1-2 p. 108 - 115

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Citation Number: 7

Abstract

The large positive ρ values obtained from Me3M− ions reacting with appropriately- substituted chloroarenes (4.1±0.1, and 2.94±0.02 for M= Sn and Si, respectively) can be accounted for the presence of a strong negative charge in the transition state of the substitution reaction. These ρ values for Me3Sn− and Me3Si− nucleophilic attack on ArX provide evidence for the overall larger selectivity of the former, compared with the more ...