THE RELATIVE EASE OF REDUCTIVE CLEAVAGE OF 1,3-DIOXOLANES AND 1,3-DIOXANES IN ETHER SOLUTION BY LiAlH4–AlCl3
- 1 September 1964
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 42 (9) , 2113-2118
- https://doi.org/10.1139/v64-312
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.Keywords
This publication has 5 references indexed in Scilit:
- THE INFLUENCE OF SUBSTITUENTS ON THE EASE AND DIRECTION OF RING OPENING IN THE LiAlH4–AlCl3 REDUCTIVE CLEAVAGE OF SUBSTITUTED 1,3-DIOXOLANESCanadian Journal of Chemistry, 1964
- Reduction with Metal Hydrides. XII. Reduction of Acetals and Ketals with Lithium Aluminum Hydride-Aluminum ChlorideJournal of the American Chemical Society, 1962
- Communications Reduction of Acetals to Ethers by Means of Lithium Aluminum Hydride-Aluminum ChlorideThe Journal of Organic Chemistry, 1958
- The Evaluation of Inductive and Resonance Effects on Reactivity. I. Hydrolysis Rates of Acetals of Non-conjugated Aldehydes and Ketones1aJournal of the American Chemical Society, 1955
- The Acetolysis of Trimethylene-D-sorbitol. 2,4-Methylene-D-sorbitol and 1,3:2,4-Dimethylene-D-sorbitolJournal of the American Chemical Society, 1944