Electrophilic Substitution at Saturated Carbon. XXV. Structural Requirements for Functional Groups Centered around Second-Row Elements to Preserve Asymmetry of …

DJ Cram, RD Trepka, PS Janiak

Index: Cram,D.J. et al. Journal of the American Chemical Society, 1966 , vol. 88, # 12 p. 2749 - 2759

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Citation Number: 25

Abstract

Abstract: The stereochemical course of base-catalyzed hydrogen-deuterium exchange at asymmetric carbon has been examined in six new systems in which the intermediate carbanion is stabilized by different functional groups centered about second-row elements. The first three systems,~-CBH~~(CH~) C* HS~~ N (CH~) C~ H~, n-C6HI3 (CH3)-C* HS020CH3, and n-CeH13 (CH3) C* HP02 (C6H~), gave values of ke/ko (rate constant for ...