
TY  - JOUR
A1  - Brown, RFC 
A1  - Smith, RJ 
T1  - The rearrangement of heteroaryl nitrenes formed by pyrolysis of fused oxadiazolones at 600&#176;C
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 3
SP  - 607
EP  - 624
KW  - 
UR  - https://doi.org/10.1071/CH9720607 
N2  - Heteroaryl nitrenes were formed by pyrolysis of the corresponding ring-fused oxadiazolones at 600°/0.1-0.5 mm with short contact times. 2-Pyridyl and 3-iso-quinolyl nitrenes rearranged predominantly by ring contraction to give cyano-pyrroles and 1-cyanoisoindole, respectively. 2-Quinolyl and 1-isoquinolyl nitrenes underwent ring fission followed by rearrangements which led to O-cyanophenyl-acetonitrile and 4-cyanoindole. 2-Benzo[f]quinolyl nitrene rearranged predominantly by ring fission, but some ring contraction also occurred. The rearrangement of 2-quinolyl nitrene has been investigated by using 14C and 15N labelling. The dominance of ring contraction or ring fission reactions is rationalized in terms of the effect on the whole &#960;-system of the localization of &#960;-electrons in an electrocyclic transition state for ring contraction. 
ER  -

