Science of Synthesis

Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 48.

Certain stable azo compounds (R1N=NR2) are decomposed in the presence of nitrogen dioxide to give nitro compounds (‌Scheme 55‌). Better yields are obtained using nitrogen dioxide that contains a catalytic amount of nitric oxide, which has a better ability to trap alkyl radicals. The reaction thus proceeds via a nitrosoalkane intermediate.[‌216‌]

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