Canadian Journal of Chemistry

The Influence of Heteroatom-substituted Methyl Groups and of Vinyl Groups (CR2= CR-) Attached to C-2 of 1, 3-Dioxolanes on the Ease and Direction of …

HA Davis, RK Brown

Index: Davis,H.A.; Brown,R.K. Canadian Journal of Chemistry, 1971 , vol. 49, p. 2563 - 2577

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Citation Number: 13

Abstract

Heteroatom substituents on the methyl group of 2-methyl-1, 3-dioxolane retard the rate of hydrogenolysis by AlH2Cl of ether solutions of the 2-substituted 1, 3-dioxolanes. The effectiveness of the heteroatoms in decreasing the ease of hydrogenolysis is H< S< O< Br< NR2. This retardation is thought to be due to the destabilization of the transition state leading to the intermediate oxocarbonium ion, caused by the electronegativity of the heteroatom ...