The formation of halogenated succinates by liquid-phase direct fluorination with elemental fluorine

Article abstract of DOI:10.1016/0022-1139(93)02975-K

Direct fluorination of maleic anhydride with elemental fluorine has been investigated in different solvents at low temperatures.It was discovered that the net conversion of maleic anhydride, as well as the overall yield and composition of the halogenated products, depend strongly on the experimental conditions employed.Fluorinations conducted in fluorotrichloromethane, chloroform or mixtures thereof, in the presence of sodium fluoride, resulted in good yields of halogenated succinic acid derivatives: the predominant products being 2,3-dihalogenated succinic acids.Product distributions varied widely between experiments conducted at 0 deg C and -25 deg C, and also between experiments conducted in neat CHCl3 and in CFCl3/CHCl3 mixtures.Experimental details and some comments regarding the stereoselectivity of halogen addition are provided.