A photo-Favorskii ring contraction reaction: the effect of ring size

…, D Heger, P Klán, M Rubina, RS Givens

Index: Kammath, Viju Balachandran; Solomek, Tomas; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klan, Petr; Rubina, Marina; Givens, Richard S. Journal of Organic Chemistry, 2013 , vol. 78, # 5 p. 1718 - 1729

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Citation Number: 10

Abstract

The effect of ring size on the photo-Favorskii induced ring-contraction reaction of the hydroxybenzocycloalkanonyl acetate and mesylate esters (7a–d, 8a–c) has provided new insight into the mechanism of the rearrangement. By monotonically decreasing the ring size in these cyclic derivatives, the increasing ring strain imposed on the formation of the elusive bicyclic spirocyclopropanone 20 results in a divergence away from rearrangement and ...