
TY  - JOUR
A1  - Chapman, KJ 
A1  - Dyall, LK 
A1  - Frith, LK 
T1  - Oxidative cyclizations. VI. Mechanism of cyclization of N-chloro-2-nitroanilines to benzofuroxans under alkaline conditions
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1984
VL  - 37
IS  - 2
SP  - 341
EP  - 354
KW  - 
UR  - https://doi.org/10.1071/CH9840341 
N2  - An improved synthesis of N-chloro-2-nitroanilines used chlorine in CCl4 solution to halogenate the 2-nitroaniline. Treatment of these CCl4 solutions of the N-chloroamines with methanolic lithium methoxide, or potassium t-butoxide in t-butyl alcohol, produced a transient red colour, and quantitative yields of the corresponding benzofuroxan (benzofurazan 1-oxide) were obtained. U.v. and e.s.r. spectra indicated that the red species is the conjugate base of the N-chloroamine. On the basis of rate measurements, it is concluded that this red anion ejects chloride ion irreversibly to yield a singlet ortho-nitrophenylnitrene, which then rapidly cyclizes to the benzofuroxan. The ortho-nitro group does not assist in chloride ion ejection. 
ER  -

