Thionation of N-Methyl- and N-Unsubstituted Thiazolidine Enaminones (2004)
AuthorsMarkovic, R., Rasovic, A., Baranac, M., Stojanovic, M., Steel, P.J., Jovetic, S.show all
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.
CitationMarkovic, 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.
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