76937-39-8Relevant articles and documents
REACTIONS OF CHLORINE MONOFLUORIDE. ELECTROPHILIC ADDITION OF CHLORINE MONOFLUORIDE TO SUBSTITUTED ALKENES
Boguslavskaya, L. S.,Chuvatkin, N. N.,Panteleeva, I. Yu.,Ternovskoi, L. A.,Krom, E. N.
, p. 2155 - 2162 (2007/10/02)
The addition reactions of the interhalogen ClF to certain derivatives of allyl alcohol CH2=CHCH2OC(O)R (R = H, CCl3, OCH3) and substituted α,β-unsaturated acids CHR=CR'C(O)R'' (R = H, Cl, CH3, COOCH3; R' = H, F, CH3; R'' = Cl, OCH3) were investigated.The presence of several electron-withdrawing substituents at the multiple bond of the alkene hinders the addition of ClF in an inert medium.Such alkenes are chlorofluorinated readily in anhydrous hydrogen fluoride.The addition of ClF is more regioselective in hydrogen fluoride than in an inert solvent.Chlorofluorination of E- and Z-1,3-dichloropropenes and dimethyl maleate and fumarate i s trans-stereospecific both in chloroform and in liquid hydrogen fluoride.The observed facts favor an electrophilic mechanism for chlorofluorination of the investigated alkenes.