Pyridinium halides as reagents: ring fission modes in. alpha.-cyclopropyl ketones and oximes

E Giacomini, MA Loreto, L Pellacani…

Index: Giacomini, E.; Loreto, M.A.; Pellacani, L.; Tardella, P.A. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 519 - 522

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Citation Number: 16

Abstract

Among the substrates we tested (1, 6, 9, 19, and 22), bicyclo [4.1. 0] heptan-2-one (6) and 1- acetylbicyclo [4.1. 0]-heptane (19) gave a selective ring fission reaction, while other substrates (1 and 9) gave products coming from the two possible modes of cyclopropyl ring fission (Table I). Clearly this point is a limiting factor for the synthetic scope of this reaction, although, in most cases, a satisfactory chromatographic separation of the two chloro ...