A theoretical study of photoinduced ring-isomerization of 3-amino-5-methyl- and 3-amino-5-phenyl-1,2,4-oxadiazoles is reported. The results well agree with the reported experimental data: in particular, they explain the ring-photoisomerization into the corresponding 2-amino-1,3,4-oxadiazoles through a ring contraction-ring expansion route; moreover, the occurrence of competing pathways involving both the ring contraction and the internal cyclization–isomerization mechanism during irradiation of the 5-alkyl substituted substrates in the presence of a base has been also substantiated.
BUSCEMI S, DAURIA M, PACE A, PIBIRI I, VIVONA N (2004). Theoretical study of photoinduced ring-isomerization in the 1,2,4-oxadiazole series. TETRAHEDRON, 60(14), 3243-3249 [10.1016/j.tet.2004.02.007].
Theoretical study of photoinduced ring-isomerization in the 1,2,4-oxadiazole series
BUSCEMI, Silvestre;PACE, Andrea;PIBIRI, Ivana;VIVONA, Nicolo'
2004-01-01
Abstract
A theoretical study of photoinduced ring-isomerization of 3-amino-5-methyl- and 3-amino-5-phenyl-1,2,4-oxadiazoles is reported. The results well agree with the reported experimental data: in particular, they explain the ring-photoisomerization into the corresponding 2-amino-1,3,4-oxadiazoles through a ring contraction-ring expansion route; moreover, the occurrence of competing pathways involving both the ring contraction and the internal cyclization–isomerization mechanism during irradiation of the 5-alkyl substituted substrates in the presence of a base has been also substantiated.File | Dimensione | Formato | |
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