Thermal racemization of allylic sulfoxides and interconversion of allylic sulfoxides and sulfenates. Mechanism and stereochemistry

P Bickart, FW Carson, J Jacobus…

文献索引：Bickart,P. et al. Journal of the American Chemical Society, 1968 , vol. 90, p. 4869 - 4876

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被引用次数: 230

摘要

Abstract: The thermal racemization of optically active allyl sulfoxides has been shown on the basis of kinetic evidence and labeling experiments to proceed by way of a facile, reversible, and wholly concerted rearrangement to optically inactive allyl sulfenates. The reaction involves an intramolecular cyclic a, y shift of the allyl group between the sulfoxide oxygen and sulfur termini. Rearrangement of (S)-a-methylallyl p-toluenesulfenate to (S)-trans- ...