Thermal and photochemical racemization of chiral aromatic sulfoxides via the intermediacy of sulfoxide radical cations.
Efficient racemization of enantiomerically pure methyl aryl sulfoxides was obtained by N-methylquinolinium tetrafluoborate (NMQ+) sensitized photolysis and by one-electron oxidation catalyzed by tris(2,2'-bipyridyl)ruthenium(III) hexafluorophosphate.
Aurisicchio
Claudia
C
Dipartimento di Chimica and Istituto di Metodologie Chimiche, Sezione Meccanismi di Reazione c/o Dipartimento di Chimica, Università degli Studi di Roma La Sapienza, Rome, Italy.
Baciocchi
Enrico
E
Gerini
Maria Francesca
MF
Lanzalunga
Osvaldo
O
D002384:Catalysis; D002412:Cations / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D017319:Photosensitizing Agents / Q000737:chemistry; D017975:Ruthenium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
D002412:Cations; D005609:Free Radicals; D017319:Photosensitizing Agents; D017975:Ruthenium Compounds; D013454:Sulfoxides