Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones

Autor: STANKA JOVETIC, PETER J. STEEL, MILOVAN STOJANOVIC, MARIJA BARANAC, ALEKSANDAR RASOVIC, RADE MARKOVIC
Jazyk: angličtina
Rok vydání: 2004
Předmět:
Zdroj: Journal of the Serbian Chemical Society, Vol 69, Iss 11, Pp 909-918 (2004)
Druh dokumentu: article
ISSN: 0352-5139
Popis: The potential of directional non-bonded 1,5-type S...O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3al4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step.
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