880104-97-2Relevant academic research and scientific papers
Intramolecular homolytic substitution of sulfinates and sulfinamides
Coulomb, Julien,Certal, Victor,Larraufie, Marie-Helene,Ollivier, Cyril,Corbet, Jean-Pierre,Mignani, Gerard,Fensterbank, Louis,Lacote, Emmanuel,Malacria, Max
supporting information; experimental part, p. 10225 - 10232 (2010/04/05)
A general and efficient method for the synthesis of cyclic sulfi-nates and sulfinamides based on intra-molecular homolytic substitution (SHi) at the sulfur atom by aryl or alkyl radi-cals is described. Both alkyl and benzo-fused compounds can be accessed di-rectly from easily prepared acyclic pre-cursors. Enantiomerically enriched sulfur-based heterocycles were formed through an SHi process with inversion of configuration at the sulfur atom. Cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the size of the incoming radical. 2-Pyridyl and 2-qui-nolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution.
Formation of cyclic sulfinates and sulfinamides through homolytic substitution at the sulfur atom
Coulomb, Julien,Certal, Victor,Fensterbank, Louis,Lacote, Emmanuel,Malacria, Max
, p. 633 - 637 (2007/10/03)
(Chemical Equation Presented) Ring road: Cyclic sulfinates and sulfinamides can be synthesized by homolytic substitution to give alkyl and benzofused families of compounds. The presence of an additional heteroatom in the ring allows the preparation of sulfur-based heterocycles that are useful synthetic intermediates (see scheme). The stereogenic sulfur atom transfers its chirality to prochiral radicals. TTMSS = tris(trimethylsilyl)silane, AIBN = azobisisobutyronitrile.
