Cyclopropyl solvolyses. IV. Leaving group and alkyl substitution effects in monocyclic systems

WF Sliwinski, TM Su, PR Schleyer

Index: Sliwinski,W.F. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 133 - 145

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Citation Number: 42

Abstract

Abstract: The acetolysis rates of a number of alkyl-and polymethyl-substituted cyclopropyl tosylates, bromides, and chlorides have been determined. The kinetic results in all cases are consistent with stereospecific disrotatory ring opening concerted with ionization. For trans-/3- alkyl substitution the observed rates show a regular but rather modest increase in the order CH3< CzH6< i-CBH7< tert-C4H9, attributed to inductive effects. The corresponding cis ...