Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

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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.

Abstract:

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Palavras-chave: 3H-1,2-dithiole-3-thione,(E)-3-alkylidene-3H-1,2-dithiole, HSAB theory.,

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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 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_20139111275

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