Tetrahedron

A facile route to 5-alkyl-2 (3H)-furanones by photoisomerisation of enedicarbonyl compounds

M D'Auria, A De Mico, G Piancatelli, A Scettri

Index: Auria, M. D'; Mico, A. De; Piancatelly, G.; Scettry, A. Tetrahedron, 1982 , vol. 38, # 11 p. 1661 - 1666

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Citation Number: 9

Abstract

A new and useful synthesis of a title compounds is reported. They can be obtained easily by photocyclization of enedicarbonyl compounds 3 and 4. A different behaviour, ascribed to the geometry of a double bond, is observed; 3 are converted only to butenolides 5, while trans- isomers 4 are converted into alkyl-furyl-ketones 5 and 6. A possible mechanism is described.