
TY  - JOUR
A1  - Dyall, LK 
A1  - Karpa, GJ 
T1  - Pyrolysis of Aryl Azides. VIII. Hammett Correlations of Rates of Pyrolysis of Substituted 2-Azidobenzophenones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1988
VL  - 41
IS  - 8
SP  - 1231
EP  - 1241
KW  - 
UR  - https://doi.org/10.1071/CH9881231 
N2  - Eight 2-azidobenzophenones with 4- or 5-substituents have been pyrolysed in decalin solution to yield 3-phenyl-2,1-benzisoxazoles. Rate values at 100&#176; are correlated with the Hammett substituent constants, with respect to both the azido (A) and benzoyl (B) reaction centres , and yield the equation log k = -4.38 + 2.08&#963;-/A -1.52&#963;B. There is a similar equation for rates measured at 120&#176;. Although nitro and benzoyl differ considerably in their neighbouring group abilities in azide  pyrolyses, it is concluded that they exert their effects through the same mechanism. The results are consistent with both published variants of an electrocyclic mechanism (Dyall; Smith, Budde and Chou). 
ER  -

