Some transformations of the substitutive recyclization product obtained from tetrachlorocyclopentadiene dimer and diethylamine

1, 1a,2,3,3a,4,5-Heptachloro-N,N-diethyl-6-oxo-1,1a,3a,6-tetrahydrocyclopropa[c]pentalene-1-carboxamide reacts with hydroxide ion and N-centered nucleophiles following exclusively the Ad_NE scheme with replacement of the 4-chlorine atom. Its reactions with methylmagnesium iodide and diethyl malonate sodium salts involve simultaneous substitution, 1,2-addition at the carbonyl group, and aromatization. Oxidation of 1,1a,2,3,3a,4,5-heptachloro-N,N-diethyl-6-oxo-1,1a,3a,6-tetrahydrocyclopropa[c]pentalene-1-carboxamide with potassium permanganate under conditions of phase-transfer catalysis is accompanied by cleavage of the cyclopentenone fragment with formation of 2,3,4,5,6-pentachloro-6-diethylcarbamoylbicyclo[3.1.0]hex-3-ene-1,2-dicarboxylic acid.