title: Can the absence of solvation of neutral reagents by ionic liquids be responsible for the high reactivity in base-assisted intramolecular nucleophilic substitutions in these solvents?
abstract: [reaction: see text] The kinetics of the rearrangement of the Z-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1a) into the relevant 4-benzoylamino-2,5-diphenyl-1,2,3-triazole (2a) induced by amines have been studied in two room-temperature ionic liquids (IL-1, [BMIM][BF4] and IL-2, [BMIM][PF6]). The data collected show that the reaction occurs faster in ionic liquids than in other conventional solvents previously studied (both polar or apolar, protic or aprotic). Presumably, this could depend on their peculiar ability to minimize the strong substrate-solvent, amine-solvent and amine-amine interactions occurring in conventional solvents.
authors.affiliation: Dipartimento di Chimica Organica E. Paterno, Università degli Studi di Palermo, Viale delle Scienze, Parco d'Orleans 2, 90128 Palermo, Italy. fdanna@unipa.it
authors.forename: Francesca
authors.initials: F
authors.lastname: D'Anna
authors.forename: Vincenzo
authors.initials: V
authors.lastname: Frenna
authors.forename: Renato
authors.initials: R
authors.lastname: Noto
authors.forename: Vitalba
authors.initials: V
authors.lastname: Pace
authors.forename: Domenico
authors.initials: D
authors.lastname: Spinelli