
TY  - JOUR
A1  - Dyall, LK 
A1  - Wah, WM 
T1  - Pyrolysis of Aryl Azides. VI. Identification of Neighbouring Group Effects in Pyrolysis of Azidopyridines and Azidoquinolines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1985
VL  - 38
IS  - 7
SP  - 1045
EP  - 1059
KW  - 
UR  - https://doi.org/10.1071/CH9851045 
N2  - Although there are literature reports of anomalous behaviour on pyrolysis of ortho-nitroazido-pyridines and ortho-nitroazidoquinolines, we find that these compounds cyclize to the expected furazan 1-oxides in near-quantitative yields, and with a high degree of neighbouring group participation by the nitro group. Kinetic studies in decalin solution reveal the following rate enhancements by the ortho-nitro group: 3-azido-2-nitropyridine, 466 at least; 4-azido-3-nitropyridine, 5400; 4-azido-3,5-dinitropyridine, 640; 4-azido-3-nitroquinoline, 82.4; 5-azido-6-nitroquinoline, 27.6; 2-nitro-1-azidonaphthalene, 12.7. The unstable furazan oxide, [1,2,5] oxa-diazolo [3,4-c]pyridine 1-oxide, has now been characterized. [1,2,5] Oxadiazolo [3,4-b]pyridine 1-oxide decomposed in decalin at 145&#176; to give products indicative of a nitrene intermediate. 
ER  -

