33579-37-2Relevant articles and documents
REACTIONS OF CHLORINE MONOFLUORIDE. REGIOSPECIFICITY AND STEREOCHEMISTRY OF THE SUBSTITUTION OF BROMINE ATOMS BY FLUORINE IN HALOGEN-SUBSTITUTED ALKANES AND ESTERS
Boguslavskaya, L. S.,Chuvatkin, N. N.,Panteleeva, I. Yu.,Ternovskoi, L. A.
, p. 814 - 820 (2007/10/02)
Under mild conditions without catalysts chlorine monofluoride substitutes bromine atoms for fluorine in bromine-substituted alkanes and esters.Electron-donating substituents promote the substitution reaction.The following sequence is observed in the reactivity of the bromine atoms at the carbon: tertiary > secondary > primary.Halogen atoms (Cl, F) at a carbon containing a bromine also promotes substitution of the latter by fluorine.The reactivity of the bromine atoms decreases in the following order: CCl2Br(CClFBr) > CHClBr(CHFBr) > CH2Br.An alkoxycarbonyl group at a carbon containing bromine prevents substitution.In a number of cases substitutive fluorination is accompanied by skeletal rearrangements and by migration of chlorine atoms.The stereochemistry of substitutive fluorination was studied for the case of the reaction of erythro- and threo-1-bromo-2-fluoro-1,2-dichloroethanes and 1,2-dibromo-1,3-dichloropropanes with chlorine monofluoride.The probable mechanism of the reaction is discussed.