title: Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.
abstract: Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
authors.affiliation: Departamento de Química, Centro de Investigación y Estudios Avanzados del IPN, Av. Instituto Politecnico Nacional 2508, San Pedro Zacatenco, 07360 Ciudad de México, Distrito Federal, Mexico, http://www.quimica.cinvestav.mx/Directorio/Investigadores/DrLujanMontelongoJesus.aspx ; Department of Chemistry and Biochemistry Duquesne University 600 Forbes Ave, Pittsburgh, PA 15202, USA, http://www.scienceresearch.duq.edu/chem/chemfac/ffleming/
authors.forename: J Armando
authors.initials: JA
authors.lastname: Lujan-Montelongo
authors.affiliation: Department of Chemistry and Biochemistry Duquesne University 600 Forbes Ave, Pittsburgh, PA 15202, USA, http://www.scienceresearch.duq.edu/chem/chemfac/ffleming/
authors.forename: Angel Ojeda
authors.initials: AO
authors.lastname: Estevez
authors.affiliation: Department of Chemistry and Biochemistry Duquesne University 600 Forbes Ave, Pittsburgh, PA 15202, USA, http://www.scienceresearch.duq.edu/chem/chemfac/ffleming/
authors.forename: Fraser F
authors.initials: FF
authors.lastname: Fleming
keywords: Isocyanides; Isonitriles; Mannich reaction; Nucleophilic addition; Sulfinates; Umpolung