A thermal fragmentation of 1, 2, 4-oxadiazole-4-oxides to nitriles and nitrosocarbonyls
P Quadrelli, G Campari, M Mella, P Caramella
Index: Quadrelli; Campari; Mella; Caramella Tetrahedron Letters, 2000 , vol. 41, # 12 p. 2019 - 2022
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Citation Number: 24
Abstract
We have recently reported that 1,2,4-oxadiazole-4-oxides 1 undergo a clean photochemical cleavage 1 to nitriles 2 and nitrosocarbonyls 3, highly reactive intermediates 2 which can be quantitatively trapped with dienes or alkenes to afford the hetero Diels–Alder (HDA) adducts 4 or the ene adducts 5 (Scheme 1). The HDA 3 and ene 4 reactions of nitrosocarbonyls have recently acquired a broad synthetic significance because of the easy manipulation of both ...
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