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

Autor:	John Crosby, Michael McPherson, R. Michael Paton, Derek J. Greig
Rok vydání:	1985
Předmět:	chemistry.chemical_classification Dimethyl acetylenedicarboxylate chemistry.chemical_compound Benzonitrile Spiro compound Double bond chemistry Nitrile Nitrilimine 1 3-Dipolar cycloaddition Organic chemistry Medicinal chemistry Cycloaddition
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1205
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19850001205
Popis:	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 CS 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::301a57b0ab672e2585c598887ba75137 https://doi.org/10.1039/p19850001205 Zobrazit plný text záznamu