REACTIONS OF NITRONES WITH SODIUM IODIDE-TRIFLUOROACETIC ANHYDRIDE SYSTEM - COMMENTS ON THE BECKMANN REARRANGEMENT OF ALDONITRONES AND COMPETITIVE PROCESSES OF NUCLEOPHILIC-ADDITION

Authors
DRABOWICZ J KOTYNSKI A KUDZIN ZH NAZARSKI RB TASZ MK
Citation
J. Drabowicz et al., REACTIONS OF NITRONES WITH SODIUM IODIDE-TRIFLUOROACETIC ANHYDRIDE SYSTEM - COMMENTS ON THE BECKMANN REARRANGEMENT OF ALDONITRONES AND COMPETITIVE PROCESSES OF NUCLEOPHILIC-ADDITION, Tetrahedron, 53(41), 1997, pp. 14169-14178
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
41
Year of publication
1997
Pages
14169 - 14178
Database
ISI
SICI code
0040-4020(1997)53:41<14169:RONWSI>2.0.ZU;2-3
Abstract
The systematic studies of the reaction of aldonitrones with the NaI-TF AA system were performed. The reaction engaged was recognised as a pre viously known process called 'the Beckmann rearrangement of nitrones'. Some mechanistic considerations on this transformation and competitiv e nucleophilic additions are presented in order to explain the origin of iodine release and its observed stoichiometry as a ell as of some p roducts isolation. The intermediacy of C-and N-iodo species (including iodonium cations) in the presence of iodide anions, is postulated. (C ) 1997 Elsevier Science Ltd.