title: Unexpected reaction of beta-cyclodextrin tosylate with pyrrolidinones.
abstract: Substitution reactions of 6I-O-p-tolylsulfonylcyclomaltoheptaose with alkyl- and arylamines in 1-methyl-2-pyrrolidinone and various pyrrolidinones were investigated. An unexpected reaction of the tosyl group with pyrrolidinones was observed resulting in products deriving from nucleophilic attack by the lactam carbonyl oxygen and further opening of the heterocyclic ring. The new compounds have been fully characterized by ESIMS and NMR analyses.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy. angela@dcci.unipi.it
authors.forename: Angela
authors.initials: A
authors.lastname: Cuzzola
authors.forename: Laura
authors.initials: L
authors.lastname: Panelli
authors.forename: Andrea
authors.initials: A
authors.lastname: Raffaelli
authors.forename: Gloria
authors.initials: G
authors.lastname: Uccello-Barretta
authors.forename: Federica
authors.initials: F
authors.lastname: Balzano
authors.forename: Piero
authors.initials: P
authors.lastname: Salvadori
mesh_terms: D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D011760:Pyrrolidinones; D047392:beta-Cyclodextrins