Use of Samarium Diiodide as an Alternative to Sodium/Mercury Amalgam in the Julia-Lythgoe Olefination

Gary E. Keck*, Kenneth A. Savin and Michael Weglarz

*Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, Email: keckchem.utah.edu

G. E. Keck, K. A. Savin, M. Weglarz, J. Org. Chem., 1995, 60, 3194-3204.

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Abstract

The use of SmI₂ in the reductive elimination of 1,2-acetoxy sulfones (Julia-Lythgoe olefination) and the reductive cleavage of vinyl sulfones is reported. A mechanistic study revealed some of the intricacies of the SmI₂-promoted Julia-Lythgoe olefination. The classical Na/Hg reductive method was also examined, and an alternative mechanism was proposed.

see article for more examples

see article for more reactions

originally proposed mechanism for the Julia-Lythgoe reduction (M = Na, SmI₂)

alternative mechanism for the Na/Hg reductive cleavage of acetoxy sulfones

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Key Words

Julia olefination, Sulfones, Samarium Diiodide

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ID: J42-Y1995-310