Ring transformation of (4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitriles to 3-haloisothiazole-5-carbonitriles

Autor:	Kalogirou, Andreas S., Christoforou, Irene C., Ioannidou, Heraklidia A., Manos, Manolis J., Koutentis, Panayiotis Andreas
Přispěvatelé:	Koutentis, Panayiotis Andreas [0000-0002-4652-7567], Christoforou, Irene C. [0000-0001-6624-3548], Kalogirou, Andreas S. [0000-0002-5476-5805]
Rok vydání:	2014
Předmět:	Acetonitriles Stereochemistry General Chemical Engineering General Chemistry Ring (chemistry) Medicinal chemistry Transformation (music) Ethylene chemistry.chemical_compound chemistry Ring transformation Single crystal x-ray structures Side products Acetonitrile Single crystal
Zdroj:	RSC Advances RSC Adv.
ISSN:	2046-2069
DOI:	10.1039/c3ra47261b
Popis:	Ring transformation of readily prepared (4-chloro-5H-1,2,3-dithiazol-5- ylidene)acetonitriles afford 3-haloisothiazole-5-carbonitriles in good to excellent yields. The transformation can be mediated using HBr (g), HCl (g) or BnEt3NCl. Mechanisms for the transformations are discussed, together with rationalizations for the formation of side products. Furthermore, single crystal X-ray structures are provided for (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5- ylidene)acetonitrile and (E)-2-bromo-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene) acetonitrile confirming the stereochemistry of the exocyclic ethene bond. © 2014 The Royal Society of Chemistry. 4 15 7735 7748 Cited By :6
Databáze:	OpenAIRE
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