Stereochemically Probing the Photo-Favorskii Rearrangement: A Mechanistic Investigation

RS Givens, M Rubina, KF Stensrud

Index: Givens, Richard S.; Rubina, Marina; Stensrud, Kenneth F. Journal of Organic Chemistry, 2013 , vol. 78, # 5 p. 1709 - 1717

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Citation Number: 4

Abstract

Using model (R)-2-acetyl-2-phenyl acetate esters of (S)-or (R)-α-substituted-p- hydroxybutyrophenones (S, R)-12a and (R, R)-12b, we have shown that a highly efficient photo-Favorskii rearrangement proceeds through a series of intermediates to form racemic rearrangement products. The stereogenic methine on the photoproduct, rac-2-(p- hydroxyphenyl) propanoic acid (rac-9), is formed by closure of a phenoxy-allyloxy ...