CLAY-CATALYZED THIOALKYLATION OF THIOPHENES AND BENZO[b]THIOPHENES

Autor:	Alex Primak, S. T. E. Mesher, Peter D. Clark
Rok vydání:	1996
Předmět:	Tris Chemistry Organic Chemistry Biochemistry Medicinal chemistry Autoclave Catalysis Inorganic Chemistry chemistry.chemical_compound Montmorillonite Chlorobenzene Yield (chemistry) Thiophene Organic chemistry Dimethyl disulfide
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 114:99-108
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426509608046415
Popis:	A method for the direct thioalkylation of thiophene (1) and benzo[b]thiophene (7) by reaction of either heterocycle with an alkyldisulfide using a ZnCl2-modified montmorillonite clay catalyst is described. The clay-catalyzed reaction of 1 with excess dimethyl disulfide (DMDS) over 24 hours in refluxing chlorobenzene yielded a mixture of bis-, tris-, and tetrakis(methylthio)thiophenes (2–5) from which 2,3,5-tris(methylthio)thiophene (4a) and tetrakis(methylthio)thiophene (5) could be isolated in modest yield. Prolonging the reaction time gave (4a) and 5 in isolated yields of 21 and 16% respectively. Carrying out the same reaction in a sealed autoclave at 150°C with an air overpressure resulted in a clean and rapid (5 h) conversion of thiophene to the tetramethylthio-derivative 5 in moderate isolated yield (50%). In a similar manner 7 could be converted to 2,3-bis(methylthio)benzo[b]thiophene (8a) or 2,3,6-tris- and 2,3,6,7-tetrakis(methylthio) derivatives 9 and 10a by clay catalyzed reactions with...
Databáze:	OpenAIRE
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