157-16-4Relevant articles and documents
GAS-PHASE REACTIONS. 36. PYROLYSIS OF VINYL AZIDE.
Bock,Dammel,Aygen
, p. 7681 - 7685 (1983)
The gas-phase pyrolyses of vinyl azide as well as of 1H-1,2,3-triazole have been investigated by means of PE spectroscopy. In accordance with predictions from MNDO hypersurface studies, vinyl azide in its lowest thermal decomposition channel splits off nitrogen to yield predominantly 2H-azirine as identified by the PE spectrum of the cool-trapped compound, which at higher temperatures rearranges to the most stable C//2H//3N isomer, acetonitrile. The experimental observations and the quantum chemical calculations both indicate that among those reaction pathways, which can readily be characterized by a suitably selected pair of reaction coordinates from the 12-dimensional hyperspace for the C//2H//3N moiety, synchronous nitrogen extrusion-azirine ring formation is the energetically most favorable one.
Hydrogen Cyanide N-Methylide: Preparation, Spectroscopic Identification, and Its Relationship to Other C2H3N Isomers
Maier, Guenther,Schmidt, Christiane,Reisenauer, Hans Peter,Endlein, Edgar,Becker, Dieter
, p. 2337 - 2352 (2007/10/02)
With the intention of isolating 1H-azirene (8) we studied several precursors which should offer an entry into the C2H3N potential energy hypersurface.It was found that in addition to the known isomers 1, 2, 3, and 6 hydrogen cyanide N-methylide (5) - and probably aminoacetylene (4) - can be detected in an argon matrix at 10 K.No spectroscopic evidence for the formation of 1H-azirene (8) was found.In other words, the first six members 1-6 are now all identified.The elucidation of the structure of the new C2H3N species is based on the comparison of the observed IR spectra with those calculated by ab initio methods. - Key Words: Matrix isolation/ Calculations, ab initio/ Flash pyrolysis/ Photochemistry/ Hydrogen cyanide N-methylide
SYNTHESE D'IMINES CYCLIQUES NON-STABILISEES PAR REACTIONS GAZ-SOLIDE SOUS VIDE ET THERMOLYSE-ECLAIR (1,2).
Guillemin, Jean-Claude,Denis, Jean-Marc,Lasne, Marie-Claire,Ripoll, Jean-Louis
, p. 4447 - 4456 (2007/10/02)
Unstabilized cyclic imines 1-4 were synthetized in gram-scale by vacuum dehydrochlorination of N-chlorocycloamines.Azirine 5 was prepared by flash vacuum thermolysis of the corresponding vinylazide 19.All the new compounds were characterized at low temperature by 1H, 13C NMR and IR spectroscopy.