Reaction of singlet oxygen with thioanisole in ionic liquids: a solvent induced mechanistic dichotomy.
A study of the reaction of thioanisole with singlet oxygen in pyrrolidinium- and imidazolium-based ionic liquids has been carried out. In these solvents, thioanisole shows a strongly enhanced reactivity with respect to molecular aprotic solvents, probably due to a stabilization of the persulfoxide intermediate in the ionic medium. Product isotope effects suggest a mechanistic change ongoing from pyrrolidinium to imidazolium solvents.
Baciocchi
Enrico
E
Istituto CNR di Metodologie Chimiche-IMC, Sezione Meccanismi di Reazione c/o Dipartimento di Chimica, Sapienza Universita di Roma, P.le A. Moro 5, 00185 Rome, Italy. enrico.baciocchi@uniroma1.it
Chiappe
Cinzia
C
Del Giacco
Tiziana
T
Fasciani
Chiara
C
Lanzalunga
Osvaldo
O
Lapi
Andrea
A
Melai
Bernardo
B