THE REDUCTIVE CLEAVAGE OF 1,3-OXATHIOLANES WITH LITHIUM ALUMINUM HYDRIDE IN THE PRESENCE OF ALUMINUM CHLORIDE OR BORON TRIFLUORIDE
- 1 October 1963
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 41 (10) , 2671-2682
- https://doi.org/10.1139/v63-388
Abstract
A number of 1,3-oxathiolanes and 1,3-dithiolanes were subjected to reduction in ether solution by lithium aluminum hydride in the presence of either aluminum chloride or boron trifluoride. Both of these Lewis acids not only isomerized 1,3-oxathiolanes but also catalyzed their hydrogenolysis to the hydroxy thioethers. Under the same conditions neither aluminum chloride nor boron trifluoride had any effect upon 1,3-dithiolanes. However, in methylene chloride solution, 1,3-dithiolanes are isomerized by both Lewis acids although their hydrogenolysis was not achieved, probably due to the insolubility of the hydride in methylene chloride.A mechanistic interpretation is discussed to explain the results obtained.Keywords
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