REACTIONS OF 1,2,5-THIADIAZOLE-3,4-DICARBONITRILE

The known compound 1,2,5-thiadiazole-3,4-dicarbonitrile, la preferentially forms mono addition compounds 3, but also bis-addition compounds 4 with oxygen, nitrogen and sulfur nucleophiles. One preparation of 1a produced bis[4-cyano-1,2,5-thiadiazol-3-ylmethyl(imino)]amine 2 as a minor product. The s...

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Published inActa chemica Scandinavica (Copenhagen. 1989) Vol. 48; no. 4; pp. 372 - 376
Main Authors MORKVED, EH, KJOSEN, H, NESET, SM
Format Journal Article
LanguageEnglish
Published COPENHAGEN Wiley 1994
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Multidisciplinary
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
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Summary:The known compound 1,2,5-thiadiazole-3,4-dicarbonitrile, la preferentially forms mono addition compounds 3, but also bis-addition compounds 4 with oxygen, nitrogen and sulfur nucleophiles. One preparation of 1a produced bis[4-cyano-1,2,5-thiadiazol-3-ylmethyl(imino)]amine 2 as a minor product. The structure of compound 2, the facile formation of triazine 5 and the monocyclic structures of 3 and 4 indicate extensive stereoelectronic interactions between vicinal substituents of 1.2,5-thiadiazole. A bicyclic diimino imide was not formed from la in sulfur- or methoxide-catalysed reactions with ammonia in methanol.
ISSN:0904-213X
DOI:10.3891/acta.chem.scand.48-0372