Steric assistance in the solvolysis of 2-alkyl-2-adamantyl p-nitrobenzoates

JL Fry, EM Engler, PVR Schleyer

Index: Fry,J.L. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 4628 - 4634

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Citation Number: 46

Abstract

Abstract: In order to estimate the relative importance of alkyl inductive and steric effects in the 2-adamantyl system, rates of solvolysis of a series of 2-alkyl-2-adamantyl p- nitrobenzoates were determined in 80 aqueous acetone. The relative first-order rate constants at 25” were: CH3, 1.0; C2H5; 7.7; CH2C (CH3) 3, 10.0; i-C3H7, 33.5; t-C4HQr 225,000. The solvolysis products are the unrearranged alcohols and exocyclic olefins, ...