Tetrahedron letters

Photocycloaddition of N-methylthiophthalimide with alkynes

JD Coyle, PA Rapley, J Kamphuis, HJT Bos

Index: Coyle, J. D.; Rapley, P. A.; Kamphuis, J.; Bos, H. J. T. Tetrahedron Letters, 1985 , vol. 26, # 18 p. 2249 - 2252

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Citation Number: 4

Abstract

Treatment of (2) with benzenesulphonic acid in ethanol under reflux provides no evidence for clean isomerisation to (3), but leads instead to a mixture of several other products. The absence of unsaturated thioketone would be in keeping with the pattern seen for thietes obtained from thioketones, where only those derived from bis-heteroatom-substituted alkynes undergo ringopening of this kind; the related oxetes obtained from ketones and ...