Thionation of N-Methyl- and N-Unsubstituted Thiazolidine Enaminones
Type of content
Journal Article
UC permalink
Publisher's DOI/URI
Thesis discipline
Degree name
Publisher
University of Canterbury. Chemistry.
Journal Title
Journal ISSN
Volume Title
Language
Date
2004
Authors
Markovic, R.
Rasovic, A.
Baranac, M.
Stojanovic, M.
Steel, P.J.
Jovetic, S.
Abstract
The potential of the directional non-bonded 1,5-type S···O interactions to initiate an incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to the functionalized 1,2-dithioles has been demonstrated. Spectral characteristics, as well as an X-ray structural analysis of the selected rearranged product, indicate that a dynamic interconversion occurs in a solution between the 1,2-dithiole and 3,3aλ⁴,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of the N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step.
Description
Citation
Markovic, R., Rasovic, A., Baranac, M., Stojanovic, M., Steel P.J. and Jovetic, S. (2004) Thionation of N-Methyl- and N-Unsubstituted Thiazolidine Enaminones. Journal of the Serbian Chemical Society, 69, pp. 909-918.
Keywords
thiazolidine, enaminone, Lawesson's reagent, 1,2-dithiole, 3,3aλ⁴,4-trithia-1-azapentalene