THE RELATIVE EASE OF REDUCTIVE CLEAVAGE OF 1, 3-DIOXOLANES AND 1, 3-DIOXANES IN ETHER SOLUTION BY LiAlH4-AlCl3

BE Leggetter, UE Diner…

Index: Leggetter,B.E. et al. Canadian Journal of Chemistry, 1964 , vol. 42, p. 2113 - 2118

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Citation Number: 7

Abstract

In ether solution, 1, 3-dioxolanes are hydrogenolyzed faster by LiAlH4-AlCl3 than are the corresponding 1, 3-dioxanes. This difference is attributed to the relative ease of oxocarbonium ion formation in the rate-determining step of the reaction. The results obtained have been utilized to explain the selective cleavage of the five-and six-membered acetal structures found in the polyacetals of hexitols.