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1,4‐Dithiafulvene aus der Umsetzung von 4,4‐disubstituierten 1,3‐Thiazol‐5(4 H )‐thionen mit Acetylenderivaten
Author(s) -
Jenny Christjohannes,
Heimgartner Heinz
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690223
Subject(s) - chemistry , aryne , medicinal chemistry , yield (engineering) , toluene , nitrile , organic chemistry , materials science , metallurgy
1,4‐Dithiafulvenes, Products of the Reaction of 4,4‐Disubstituted 1,3‐Thiazol‐5(4 H )‐thiones and Acetylenic Compounds On heating in toluene, 4,4‐disubstituted 1,3‐thiazol‐5(4 H )‐thiones 1 and acetylenecarboxylates or acetylenecarbonitriles 2 undergo a cyclosubstitution reaction to yield 2‐methylidene‐1,3‐dithiol derivatives 3 (1,4‐dithiafulvenes) and a nitrile. Further heating of 3a and 3b in the presence of excess 2a leads to the isomeric 2,3‐dihydrothiophene‐2‐thiones 4a and 4b , respectively. The benzodithiafulvene 14 has been formed in a similar reaction from 1a and in situ generate benzyne.