Issue 0, 1985
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Cycloaddition reactions of 1,4,2-dithiazole-5-thiones

Derek J. Greig,   Michael McPherson,   R. Michael Paton  and  John Crosby  

Abstract

1,4,2-Dithiazole-5-thiones can act either as the 2-atom or the 3-atom component in 2 + 3-cycloadditions. Benzonitrile N-phenylimine, generated in situ by dehydrochlorination of N-phenylbenzohydrazonoyl chloride, reacts at the exocyclic C[double bond, length half m-dash]S double bond forming the thiadiazolethione (17) and the spiro compound (18) by collapse of the initial cycloadduct (19) and further 1,3-dipolar cycloaddition. The corresponding reaction with ethyl azidoformate yields a 5-ethoxycarbonylimino-1,4,2-dithiazole. On treatment with dimethyl acetylenedicarboxylate and ethyl cyanoformate the dithiazolethione itself acts as a 1,3-dipole forming 1,3-dithiole and 1,4,2-dithiazole thiones with expulsion of a nitrile fragment.

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Article information

DOI
https://doi.org/10.1039/P19850001205
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1985, 1205-1208

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Cycloaddition reactions of 1,4,2-dithiazole-5-thiones

D. J. Greig, M. McPherson, R. M. Paton and J. Crosby, J. Chem. Soc., Perkin Trans. 1, 1985, 1205 DOI: 10.1039/P19850001205

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