
TY  - JOUR
A1  - Boshev, G 
A1  - Dyall, LK 
A1  - Sadler, PR 
T1  - Pyrolysis of aryl azides. II. Naphthyl azides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 3
SP  - 599
EP  - 606
KW  - 
UR  - https://doi.org/10.1071/CH9720599 
N2  - Kinetic studies of the pyrolyses of 1- and 2-naphthyl azides reveal neighbouring group participation by nitro and phenylazo substituents. The acceleration observed in 1-nitro-2-naphthyl azide, 1-phenylazo-2-naphthyl azide, and 2-nitro-1-naphthyl azide is 1730-, 211-, and 23.6-fold, respectively, in nitrobenzene solution at 120º. These effects are all smaller than that of the 2-nitro group in phenyl azide (3370-fold), which is ascribed to the steric effect of the peri hydrogen at C8 in naphthyl azides. The sizes of these neighbouring group effects correlate with the success of oxidative cyclization of ortho-substituted naphthylamines with (diacetoxyiodo)benzene. 
ER  -

