Kinetics of the reaction of. beta.-methoxy-. alpha.-nitrostilbene with thiolate ions. First direct observation of the intermediate in a nucleophilic vinylic substitution

CF Bernasconi, RB Killion Jr, J Fassberg…

Index: Bernasconi, Claude F.; Killion, Robert B.; Fassberg, Julianne; Rappoport, Zvi Journal of the American Chemical Society, 1989 , vol. 111, # 17 p. 6862 - 6864

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Citation Number: 27

Abstract

Upon mixing 4 with RS-a rapid reaction is observed, which leads to a species whose absorption spectrum is distinctly different from that of 4 and 6 (Figure 1). The similarity of this spectrum to that of thiolate ion adducts of a-nitros til bene^^ and the fact that the intermediate slowly converts to 6 constitute strong evidence that the intermediate is 5. The kinetics of intermediate formation and conversion to products were measured separately. Rates of ...