Unexpected reaction of beta-cyclodextrin tosylate with pyrrolidinones.
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.
Cuzzola
Angela
A
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy. angela@dcci.unipi.it
Panelli
Laura
L
Raffaelli
Andrea
A
Uccello-Barretta
Gloria
G
Balzano
Federica
F
Salvadori
Piero
P
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*
D011760:Pyrrolidinones; D047392:beta-Cyclodextrins