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Paper | Regular issue | Vol 71, No. 7, 2007, pp.1529-1537
Published online, 8th May, 2007
DOI: 10.3987/COM-07-11040
On the Photoreaction of Some 1,2,4-Oxadiazoles in the Presence of 2,3-Dimethyl-2-butene. Synthesis of N-Imidoylaziridines

Antonio Palumbo Piccionello, Ivana Pibiri, Andrea Pace, Rosa Angela Raccuglia, Silvestre Buscemi, Nicolò Vivona,* and Gianluca Giorgi

*Dipartimento di Chimica Organica “E. Paterno”, Universita degli Studi di Palermo, Viale delle Scienze-Parco d’Orleans II, I-90128, Palermo, taly


The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of 2,3-dimethyl-2-butene has been investigated. The irradiation in acetonitrile yielded differently substituted N-imidoyl-aziridines through an aziridination reaction involving an acyliminonitrene intermediate. Pyrolysis of N-imidoyl-aziridines produced the corresponding N-allylamidines through a ring opening process.