NN-dichloroperfluoroaniline

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Abstract
NN-Dichloroperfluoroaniline has been prepared by chloronation of perfluoroaniline with t-butyl hypochlorite. It oxidises iodide ion to iodine, converts anisole into a mixture of o- and p-chloroanisole, yields perfluoroazobenzene when pyrolysed, and rearranges to N,4-dichloropentafluorocyclohexa-2,5-dienylideneamine when treated with a catalytic quantity of iodine. The N-chloro-imine gives a 1 : 4 adduct with bistrifluoromethyl nitroxide and a 1 : 1 Diels–Alder adduct with cyclopentadiene, and provides 4-chloropentafluorocyclohexa-2,5-dienone and a compound believed to be 3,4-dichlorotetrafluorocyclohexa-2,5-dienone when hydrolysed with hydrochloric acid.

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