The reaction of 2,4-diphenyl-4,5-dihydro-1,3-oxazol-5-one 1 with 4-phenyl-N-tosyl-1-azabuta-1,3-diene 2 has been investigated using different experimental conditions. Whereas at room temperature the kinetically controlled Michael adduct 3 was isolated, at 110°C products 4, 5, 6 and 7 were obtained. Their formation is explained according to 1,3-dipolar cycloaddition and nucleophilic addition, both related to the dual nature of the azlactone 1. The reactivity of azlactone 1 towards imine 2, which is different from that observed with N-alkyl- and N-aryl-1-azabuta-1,3-dienes, is explained on the basis of the electronic effects exerted by the tosyl substituent.
Reaction of 2,4-diphenyl-4,5-dihydro-1,3-oxazol-5-one with 4-phenyl-N-tosyl-1-azabuta-1,3-diene : C=C versus C=N double bond addition / P. Dalla Croce, R. Ferraccioli, C. La Rosa. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :17(1994), pp. 2499-2502.
Titolo: | Reaction of 2,4-diphenyl-4,5-dihydro-1,3-oxazol-5-one with 4-phenyl-N-tosyl-1-azabuta-1,3-diene : C=C versus C=N double bond addition |
Autori: | DALLA CROCE, PIERO (Primo) LA ROSA, CONCETTA (Ultimo) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1994 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1039/P19940002499 |
Appare nelle tipologie: | 01 - Articolo su periodico |