Some transformations of the substitutive recyclization product obtained from tetrachlorocyclopentadiene dimer and diethylamine |
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Authors: | F. A. Gimalova O. A. Gavrilov S. A. Torosyan M. S. Miftakhov |
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Affiliation: | (1) Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia |
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Abstract: | 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 AdNE 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. |
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