Tetrahedron

Photochemistry of phthaloylcysteine, its methyl ester and C-unprotected S-alkyl derivatives

AG Griesbeck, J Hirt, W Kramer, P Dallakian

Index: Griesbeck, Axel G.; Hirt, Joachim; Kramer, Wolfgang; Dallakian, Paul Tetrahedron, 1998 , vol. 54, # 13 p. 3169 - 3180

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Citation Number: 40

Abstract

N-Phthaloyl cysteine derivatives 1a-d were photochemically transformed by elimination, decarboxylation, and via electron transfer cyclization to the products 2, 3, 4 and 6–8. The spin selectivities of singlet and triplet pathways were investigated in acetonitrile and acetone. The excited singlets were prone to elimination and γ-H abstractions (eg formation of 5) whereas the triplets cyclized to thiazinoisoindoles. This behaviour can be correlated ...