Rates of Solvolysis of the Alkylphenyldimethylcarbinyl Chlorides. Evidence for the Importance of Carbon-to-Carbon Hyperconjugative Contributions in Alkyl Groups1, …

HC Brown, JD Brady, M Grayson…

Index: Brown et al. Journal of the American Chemical Society, 1957 , vol. 79, p. 1897,1900

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Citation Number: 59

Abstract

Phenyldimethylcarbinol and its o-, m-and p-monoalkyl (methyl, ethyl, isopropyl and t-butyl) derivatives were synthesized. With one exception, these carbinols were converted readily to the corresponding tertiary chlorides by treatment with hydrogen chloride. The failure of ot- butylphenyldimethylcarbinol to yield the expected tertiary chloride is attributed to the large strains to be expected in this molecule, a homomorph of the unknown o-di-t-butylbenzene. ...