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.
Reaction of Singlet Oxygen with Thioanisole in Ionic Liquids: a Solvent Induced Mechanistic Dichotomy / Baciocchi, Enrico; Cinzia, Chiappe; Tiziana Del, Giacco; Fasciani, Chiara; Lanzalunga, Osvaldo; Lapi, Andrea; Bernardo, Melai. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 11:6(2009), pp. 1413-1416. [10.1021/ol900140w]
Reaction of Singlet Oxygen with Thioanisole in Ionic Liquids: a Solvent Induced Mechanistic Dichotomy
BACIOCCHI, Enrico;FASCIANI, CHIARA;LANZALUNGA, Osvaldo;LAPI, Andrea;
2009
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.