Apparent carbon-carbon bond cleavage in an epoxide. 2,3,4,5,6-Hexachloro-12-oxopentacyclo8,11.03,10.05,9>tridecane; a minor product from the acid treatment of endrin

Article abstract of DOI:10.1139/v82-073

The treatment of endrin (1) with sulfuric acid produces ketoendrin 2 from 6 to 8percent of another product that we show to be 2,3,4,4,5,6-hexachloro-12-oxapentacyclo<5.4.1.1.^8,11.0^3,10.0^5,9>tridecane 3, based initially on spectral evidence and confirmed by a single crystal X-ray diffraction study.The formation of 3 involves an apparent and unusual carbon-carbon single bond cleavage in an epoxide accompanied by cycloaddition to a proximate carbon-carbon double bond.This transformation probably proceeds by the route outlined in ref. 1.Some of the observed nmr parameters of 3 are discussed in the light of its structure and a comparison is made with the observed spectra for endrin (1).