ortho Effects in Reactions of Nucleophiles with Benzyl Chlorides

JF Bunnett, JD Reinheimer

Index: Bunnett,J.F.; Reinheimer,J.D. Journal of the American Chemical Society, 1962 , vol. 84, p. 3284 - 3288

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Citation Number: 19

Abstract

Rates of reactions of LiOCHs, LiSGHs, KI and (CH3) aN with benzyl chloride and its o- methyl and o-bromo derivatives have been measured; AHS and AS values have been determined. The reagents of higher polarizability (I-and CsHsS-) are especially reactive, relative to CHsO-, with substrates carrying ortho substituents of higher polarizability. London interactions in the transition state are tentatively judged to be responsible. Experimental ...