Journal of the Chemical Society. Chemical communications p. 233 - 234 (1983)
Update date:2022-08-11
Topics:
Moodie, Roy B.
Payne, Malcolm A.
Schofield, Kenneth
The title reaction effected in oleum at 150 deg C gives a quantitative yield based on chlorine of a mixture of 1,3,5-trichloro-2,4,6-trinitrobenzene and 1,2,3,5-tetrachloro-4,6-dinitrobenzene; the dependence of product ratios on acidity, effects of additives, and results of isotopic-labelling studies indicate that the latter product is formed via reversible ipso-attack of nitronium ion at a nitro substituted position followed by nucleophilic capture to give a diene which gives, possibly after oxydation, chlorine in an electrophilic form for reaction with starting material.
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