Unexpected reaction of beta-cyclodextrin tosylate with pyrrolidinones
Angela Cuzzola1, Laura Panelli, Andrea Raffaelli
1Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy. angela@dcci.unipi.it
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.
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