Elucidation of the vicarious nucleophilic substitution of hydrogen mechanism via studies of competition between substitution of hydrogen, deuterium, and fluorine

…, T Lemek, A Kwast, F Terrier

Index: Makosza, Mieczyslaw; Lemek, Tadeusz; Kwast, Andrzej; Terrier, Francois Journal of Organic Chemistry, 2002 , vol. 67, # 2 p. 394 - 400

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Citation Number: 41

Abstract

Relations of rates of the vicarious nucleophilic substitution of hydrogen (VNS) and SNAr substitution of fluorine in 2-fluoronitrobenzenes with chloroalkyl aryl sulfone carbanions were determined from competitive experiments carried out at various concentrations of base. The observed dependence of the VNS/SNAr rate ratio on the base concentration confirmed the two-step mechanism of the VNS, which consists of reversible formation of σH adducts ...