title: The singlet oxygen oxidation of chlorpromazine and some phenothiazine derivatives. Products and reaction mechanisms.
abstract: A kinetic and product study of the reactions of chlorpromazine 1, N-methylphenothiazine 2, and N-ethylphenothiazine 3 with singlet oxygen was carried out in MeOH and MeCN. 1 undergoes exclusive side-chain cleavage, whereas the reactions of 2 and 3, in MeOH, afforded only the corresponding sulfoxides. A mechanism for the reaction of 1 is proposed where the first step involves an interaction between singlet oxygen and the side-chain dimethylamino nitrogen. This explains why no side-chain cleavage is observed for 2 and 3.
authors.affiliation: Dipartimento di Chimica and Istituto CNR di Metodologie Chimiche-IMC, Sezione Meccanismi di Reazione c/o Dipartimento di Chimica, Sapienza Università di Roma, Piazzale A. Moro 5, 00185 Rome, Italy. enrico.baciocchi@uniroma1.it
authors.forename: Enrico
authors.initials: E
authors.lastname: Baciocchi
authors.forename: Tiziana
authors.initials: T
authors.lastname: Del Giacco
authors.forename: Osvaldo
authors.initials: O
authors.lastname: Lanzalunga
authors.forename: Andrea
authors.initials: A
authors.lastname: Lapi
authors.forename: Daniele
authors.initials: D
authors.lastname: Raponi
mesh_terms: D002746:Chlorpromazine / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction; D010640:Phenothiazines / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry*
chemical_list: D010640:Phenothiazines; D026082:Singlet Oxygen; D002746:Chlorpromazine