Some reactions of dieldrin and the proton magnetic resonance spectra of the products

Abstract

Derivatives of dieldrin have been prepared by reaction of the compound with hydrogen bromide and with toluene-p-sulphonic acid, by mild hydrogenation, and by irradiation with ultraviolet light. Structures are proposed for all the compounds obtained, mainly by comparing their proton magnetic resonance spectra with those of similar compounds of known structure. The acids opened the epoxide ring, the anions entering the endo-position without molecular rearrangement. Hydrogenation first removed the chlorine atom anti to the double bond and then saturated the double bond with removal of its two attendant chlorine atoms. Irradiation gave a saturated isomer by intramolecular hydrogen-transfer and cross linking.