
TY  - JOUR
A1  - Beckwith, ALJ 
A1  - Redmond, JW 
T1  - Reaction of carbethoxynitrene with anthracene, phenanthrene, and pyrene
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1966
VL  - 19
IS  - 10
SP  - 1859
EP  - 1870
KW  - 
UR  - https://doi.org/10.1071/CH9661859 
N2  - Carbethoxynitrene, generated by thermal decomposition of ethyl azido- formate, reacts with anthracene to yield a mixture of 9-, 1-, and 2-anthrylurethane. Phenanthrene when treated with carbethoxynitrene affords 9-, 1-, and 4-phenanthryl-urethane, and pyrene is similarly converted into a mixture of 1- and 4-pyrenyl- urethane. In any one substrate there is no simple relationship between the isomer ratio and free-valence numbers or bond orders. The relative yields of products are most easily rationalized in terms of a dichotomy of mechanism, the reaction proceeding both by a direct substitution pathway (electrophilic or free-radical) and via an aziridine formed by addition of carbethoxynitrene across positions of high bond order. 
ER  -

