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Alternative paths in the ring opening of oxadiaziridine: The diimide N-oxide versus the oxodiimide rearrangement
Authors:Renzo Cimiraglia  Maurizio Persico  Jacopo Tomasi
Affiliation:(1) Istituto di Chimica Fisica dell'Università di Pisa, Via Risorgimento, 35, I-56100 Pisa, Italy;(2) Laboratorio di Chimica Quantistica ed Energetica Molecolare del C.N.R., Via Risorgimento, 35, I-56100 Pisa, Italy
Abstract:The ring opening of the oxadiaziridine by cleavage of the N-N bond has been theoretically investigated by SCF calculations improved with limited CI. The possible competition of this reaction with the better known ones (N-O bond cleavage, inversion of the N atom) is discussed. The chemical implications of the formation of a new type of 1,3-dipole are examined.
Keywords:Ring opening reactions  1,3-Dipoles  Diimide N-oxide interconversion mechanisms
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