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Paper | Regular issue | Vol 34, No. 12, 1992, pp.2313-2322
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6130
Photochemical Behaviour of 1,2,5-Oxadiazoles — Irradiation of Some 3-Acylamino-1,2,5-oxadiazoles in the Presence of Nucleophiles

Silvestre Buscemi, Vincenzo Frenna, Tullio Caronna, and Nicolo Vivona*

*Dipartimento di Chimica Organica, Università di Palermo, Via Archirafi 20, 90123 Palermo, Italy


The photochemical behaviour of some 3-acylamino-1,2,5-oxadiazoles (furazans) has been investigated. On irradiation at 254 nm in the presence of nucleophiles (ammonia, primary or secondary amines), the photoreaction produced 3-substituted 1,2,4-oxadiazoles in which the substituent at C(3) arises from the used reagent. Some mechanistic considerations are reported.