Tetrahedron

A photochemical rearrangement of β, γ-unsaturated cyclic ketones

JR Williams, H Ziffer

Index: Williams,J.R.; Ziffer,H. Tetrahedron, 1968 , vol. 24, p. 6725 - 6734

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Citation Number: 25

Abstract

Irradiation of the β, γ-unsaturated cyclic ketones I and IV results in an unusual rearrangement yielding the conjugated cyclopropyl ketones IIa and Va. The structures of the photoproducts were deduced from their spectroscopic properties and proved by converting the photoproducts to compounds of known structure. The photoproduct Va has been converted to a 10α methyl A-nor steroid. A possible mechanism for the reaction is ...

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