Nucleophilic addition to olefins. Part 23. High intrinsic rate constant and large imbalances in the thiolate ion addition to substituted. alpha.-nitrostilbenes

CF Bernasconi, RB Killion

Index: Bernasconi, Claude F.; Killion, Robert B. Journal of the American Chemical Society, 1988 , vol. 110, # 22 p. 7506 - 7512

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Citation Number: 47

Abstract

Abstract: The kinetics of the reversible addition of alkyl thiolate ions (RS-with R= Et, HOCH2CH2, CH, 0COCH2CH2, and CH30COCH2) to a-nitrostilbene and of HOCH2CH2S- to a-nitrostilbene substituted in the a-phenyl ring (Z= 4-CH,, H, 4-Br, 3-NO2, and 4-N02) have been measured in 50% Me2SO-50% water at 20 OC. Brernsted@ values pig, &),