Tetrahedron

Photochemical rearrangement of α-chloro-propiophenones to α-arylpropanoic acids: studies on chirality transfer and synthesis of (S)-(+)-ibuprofen and (S)-(+)- …

HR Sonawane, NS Bellur, DG Kulkarni, NR Ayyangar

Index: Sonawane, Harikisan; Bellur, Nanjundiah S.; Kulkarni, Dilip G.; Ayyangar, Nagaraj R. Tetrahedron, 1994 , vol. 50, # 4 p. 1243 - 1260

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Citation Number: 29

Abstract

A new single-step efficient photocchemical approach for α-arylpropanoic acids (4) from α chloro-propiophenones (5) is described. It involves carbonyl triplet excited state directed 1, 2- aryl migration of the aryl group which has been found to be highly dependent upon the nature of the aryl substituent. The mode of this rearrangement is probed by the study of the photobehaviour of a set of optically active α-chloro-propiophenones. The results suggest ...