Synthesis of 1,3-dithiin dithioortho esters from the reaction of Fischer carbenes and 3H-1,2-dithiole-3-thiones

Alejandro M Granados; Jeronimo Kreiker; Rita H de Rossi; Pedro Fuertes; Tomás Torroba

doi:10.1021/jo052168e

Synthesis of 1,3-dithiin dithioortho esters from the reaction of Fischer carbenes and 3H-1,2-dithiole-3-thiones

J Org Chem. 2006 Jan 20;71(2):808-10. doi: 10.1021/jo052168e.

Authors

Alejandro M Granados¹, Jeronimo Kreiker, Rita H de Rossi, Pedro Fuertes, Tomás Torroba

Affiliation

¹ Instituto de Investigaciones en Físico Química de Córdoba (INFIQC), Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina. ale@dqo.fcq.unc.edu.ar

PMID: 16408999
DOI: 10.1021/jo052168e

Abstract

[reaction: see text] Tricyclic 4-ethyl-5-thioxo-3H,5H-bis[1,2]dithiolo[3,4-d][4,3-b]pyrrol-3-one and monocyclic 3H-1,2-dithiole-3-thione derivatives reacted with Fischer carbene complexes, giving 1,3-dithiin dithioortho esters through insertion of the carbenic carbon into the S-S bond next to the thiocarbonyl function of the substrate.