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Communication | Special issue | Vol 74, No. 1, 2007, pp.225-231
Published online, 4th December, 2007
DOI: 10.3987/COM-07-S(W)62
Conformational Biasing in 1,3-Oxidative Rearrangements of Dienols

George Majetich,* Hisaya Nishide, Ryan M. Phillips, and Jianhua Yu

*Department of Chemsitry, The University of Georgia, Athens, Georgia 30602, U.S.A.

Abstract

1-Vinyl-2-cycloalkenols are oxidized to form conjugated dienones in useful yields. Although this oxidative rearrangement is general, severe steric interactions can favor the formation of a conjugated dienal instead of a conjugated dienone. Several heterocyclic analogues were also studied.