REACTION OF BROMOTRICHLOROMETHANE DERIVED FREE-RADICALS WITH URACIL IN A MODEL SYSTEM - STRUCTURES OF PRODUCTS FORMED

Free radicals generated by benzoyl peroxide-mediated catalytic decompo sition of bromotrichloromethane (eg. trichloromethyl) were allowed to react under nitrogen or under air with uracil. Under nitrogen two reac tion products were formed, one was identified as 5-chlorouracil and th e other as a 5-bromouracil. Under air, besides the above two products other nine were also formed: 5,6-dihydrouracil; 5-hydroxyuracil; a chl orohydroxy adduct of uracil; a bromohydroxy derivative of uracil havin g the 5,6 bond in the saturated form; other bromohydroxy derivative of uracil having the double bond intact; 5,6-dihydroxyuracil; two dihalo genated hydroxylated uracil derivatives and one peak we were not able to descipher its structure. No single reaction product formed had carb on centered radicals (eg. trichloromethyl) added from CBrCl3 and conse quently would be missed in 'in vivo' covalent binding studies where C- 14 haloalkane (CBrCl3 or carbon tetrachloride) were employed. If simil ar reaction products resulted during interaction of CBrCl3 reactive me tabolites with uracil in RNAs, significant deleterious effects in thei r function would be expected. That possibility, however, remains to be established.