Isolation of Primary Decomposition Products of Azides. I. 1,4-Diphenyl5-azido-1,2,3-triazole

Preparation and Properties of Imido Intermediates (Imidogens)

“…examination of Smith's solid imido derivative (XLVII) failed to detect the presence of a triplet state (284) so that the electrons must be presumed paired.…”

New insight into experimental and theoretical properties of some para-like substituted 2-azidothiophenes

“…1 This reaction has been exploited for application in synthesis 1,2 but the details of the mechanism involved represent an intriguing question. The significantly low activation energies of thermally induced ring-cleavages of 2-azido-5-oxofurans, 3 5azidotriazoles 4 and 5-azidopyrazoles 5 have been explained either by valence-bond contributors to the presumed nitrene intermediates 3,5 or by concerted processes. 4,5b Further findings on the thermolysis of isomeric α-azidoand β-azido-thiophenes 6 (and the benzo derivatives 7 ), and α-azidoand β-azido-selenophenes, 8 suggested that the dissociation of the α-azidoheteroaryls is likely to proceed via a low-energy process involving concerted ring-opening and dinitrogen loss (path b; bЈ, Scheme 1), rather than via singlet nitrene (path a; b, R = H, X = S, Se; Scheme 1).…”

Gas phase flash pyrolysis of 3-azido-1,2,4-triazole: generation and ultraviolet photoelectron spectrum of N-cyanomethanimine

“…(b) Ring opening has been postulated or demonstrated for other heterocyclic compounds such as 5-azido-l,2,4-triazole (24) and azido pyrazole (25,26). In our case, this reaction would require the 1-3 migration of a hydrogen atom to form also 4, which renders it improbable in spite of the relative stability of 4 ( Table 1).…”