AROMATIC ALDEHYDE METHYLHYDRAZONES AND NITRILE OXIDE - CRYSTAL-STRUCTURE OF 3,6-DIPHENYL-4-METHYL-6H-1,2,4,5-OXATRIAZINE

Authors
RISITANO F GRASSI G FOTI F BRUNO G NICOLO F
Citation
F. Risitano et al., AROMATIC ALDEHYDE METHYLHYDRAZONES AND NITRILE OXIDE - CRYSTAL-STRUCTURE OF 3,6-DIPHENYL-4-METHYL-6H-1,2,4,5-OXATRIAZINE, Tetrahedron, 49(45), 1993, pp. 10427-10434
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
45
Year of publication
1993
Pages
10427 - 10434
Database
ISI
SICI code
0040-4020(1993)49:45<10427:AAMANO>2.0.ZU;2-B
Abstract
The reaction of methylhydrazones 1 with nitrile oxide has been examine d. The initial product is the Z-adduct 2, which, depending on the reac tion procedure and the substituents, can undergo either isomerization to the thermodynamically stable E-adduct 3 or tautomerization to the o xatriazine 4 or irreversible cyclization to the triazole 5. A general mechanism consistent with these results is proposed. Structure 4 was c onfirmed by X-ray studies.