This article is cited in 11 papers

Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones

V. A. Ogurtsov^a, O. A. Rakitin^a, Ch. W. Rees^b, A. A. Smolentsev<sup>a

a</sup> N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b Department of Chemistry, Imperial College London, London, UK

Abstract: The thiocarbonyl group of 4,5-dichloro-1,2-dithiole-3-thione reacts as a 1,3-dipolarophile towards diaryl nitrile imines by 1,3-dipolar cycloaddition followed by opening of the dithiole ring with loss of sulfur to give 5-methylene-1,3,4-thiadiazolines; this reaction together with nucleophilic displacement (before or after cycloaddition) of the selectively reactive 5-chlorine atom provides a rapid access to stable 5-methylene-1,3,4-thiadiazolines.

Language: English

DOI: 10.1070/MC2005v015n02ABEH002086

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