Haloalkoxylation of 3-Organyloxy-1-Propenes in Dimethylacetylenecarbinol Medium

Abstract

Reaction of alkoxyhalogenation 3-organyloxy-1-propenes with N-bromosuccinimide (or iodine) in dimethylacetylenecarbinol medium proceeds regioselectively according to NMR spectra. It proceeds at a low temperatureç cooling the reaction mixture with ordinary ice. The main reaction products, diethers -3-bromo (iodine) -1,2-propanediol, are formed in high yields. İt founded that the alkoxyhalogenation of allyl ethers with propinol proceeds regioselectively with fixation of the halogen atom to the peripheral carbon atom of C=C bond. The yields of bromine-containing products are higher than those for iodine analogues. Iodine-containing products boil at a higher temperature than bromine analogues. In the reaction products, substances with the replacement of the halogen atom with unsaturated alcohol are not observed. The reaction was monitored by means of thin layer chromatography. Similar synthesized compounds are used as biologically active compounds.