Solvolysis of haloallenes. Alkyl-substituted haloallenes

MD Schiavelli, RP Gilbert, WA Boynton…

Index: Schiavelli,M.D. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 5061 - 5064

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Citation Number: 9

Abstract

Abstract: The solvolysis of six trisubstituted haloallenes is reported. The solvent dependence and the activation parameters are found to be typical of SN1 reactions. The data are interpreted in terms of a unimolecular reaction proceeding via a charge-delocalized allenyl cation. Substitution of tert-butyl groups at the propargylic position of the cation encourages reaction at the allenyl position. The change in relative rate for phenyl substitution is ...