3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2- dithiole transformation: theoretical and experimental studies

3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2- dithiole transformation: theoretical and experimental studies

Couto, Marcos; Cabrera, Mauricio; Echeverría, Gustavo A.; Piro, Oscar E.; González, Mercedes; Cerecetto., Hugo

Abstract:

During the development of hybrid chemopreventive agents containing chalcone framework and 3H-1,2- dithiole-3-thione moiety an unexpected product was observed. When ADT-OH (Table 1) was subjected to classical alkylation conditions, working in an excess of KI and K2CO3, we have obtained the resulting product of the electrophile character of the thiocarbonyl moiety on the 3-position of the 1,2- dithiole, instead of the expected nucleophilic-reaction product. The aim of this work was rationalized this observed reactivity from an experimental and theoretical point of view.

During the development of hybrid chemopreventive agents containing chalcone framework and 3H-1,2- dithiole-3-thione moiety an unexpected product was observed. When ADT-OH (Table 1) was subjected to classical alkylation conditions, working in an excess of KI and K2CO3, we have obtained the resulting product of the electrophile character of the thiocarbonyl moiety on the 3-position of the 1,2- dithiole, instead of the expected nucleophilic-reaction product. The aim of this work was rationalized this observed reactivity from an experimental and theoretical point of view.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_20139111275

Referências bibliográficas

• [1] 1 Félix, S.; Ascenso, J.R.; Lamartine, R.; Pereira, J.L.C. Tetrahedron, 1999, 55, 8539-8546

Como citar:

Couto, Marcos; Cabrera, Mauricio; Echeverría, Gustavo A.; Piro, Oscar E.; González, Mercedes; Cerecetto., Hugo; "3H-1,2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1,2- dithiole transformation: theoretical and experimental studies", p-10-10. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20139111275