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2-Thiazolin-5-thiones, a new type of sulfur heterocycle - synthesis and reactions


Heimgartner, Heinz (1986). 2-Thiazolin-5-thiones, a new type of sulfur heterocycle - synthesis and reactions. Croatica Chemica Acta, 59(1):237-265.

Abstract

Simple syntheses of 4,4-disubstituted 2-thiazolin-5-thiones, which have so far been difficult to obtain, are described. These compounds are stable and undergo a number of different reactions. The first type of reaction discussed here are cyclosubstitutions, which occur on heating in the presence of electron-deficient acetylenes. 1,3-Dithiafulvenes are thus formed via nitrile elimination. Thiazolinthiones show different chemical behavior in reactions with ynamines. On warming, thiazolinylidene-thioamides and -thioketones are formed via a [2+2] cycloaddition, followed by an electrocyclic ring opening reaction. The third reaction type has been observed in the conversion with 1,3-dipolar reagents. In situ generated benzonitriliumbetaines undergo 1,3-dipolar cycloaddition to the exocyclic C,S-double bond and form dithiaspiro[4.4]nonadienes.

Simple syntheses of 4,4-disubstituted 2-thiazolin-5-thiones, which have so far been difficult to obtain, are described. These compounds are stable and undergo a number of different reactions. The first type of reaction discussed here are cyclosubstitutions, which occur on heating in the presence of electron-deficient acetylenes. 1,3-Dithiafulvenes are thus formed via nitrile elimination. Thiazolinthiones show different chemical behavior in reactions with ynamines. On warming, thiazolinylidene-thioamides and -thioketones are formed via a [2+2] cycloaddition, followed by an electrocyclic ring opening reaction. The third reaction type has been observed in the conversion with 1,3-dipolar reagents. In situ generated benzonitriliumbetaines undergo 1,3-dipolar cycloaddition to the exocyclic C,S-double bond and form dithiaspiro[4.4]nonadienes.

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Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1986
Deposited On:11 Jun 2014 07:07
Last Modified:05 Apr 2016 17:54
Publisher:Croatian Chemical Society
ISSN:0011-1643
Funders:Swiss National Science Foundation, Stipendienfonds der Schweizerischen Chemischen Industrie zur Unterstützung von Doktoranden auf dem Gebiet der Chemie, F. Hoffmann-La Roche & Co. AG, Basel
Free access at:Publisher DOI. An embargo period may apply.

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