CXLIX.—αβ-Dichloro-β-bromovinyl ethyl ether

The alpha-Haloalkyl Ethers

“…-Halovinyl alkyl ethers react with hydroxyl compounds on heating, without added catalyst, as shown by Imbert (188) and by Crompton and others (75,76,360). The reaction may proceed in two ways.…”

“…The polyhaloalkene may be obtained by the dehydrohalogenation of a polyhaloalkane in the same mixture. These reactions, first described by Geuther (123, 125) and by Paternd (292, 293), have been employed for both alkyl (75,76,187,188,189,190,360) and aryl rovinyl ethers (99), and of phenoxyacetylene with bromine or iodine gave the corresponding 1,2-dihalovinyl ethers (193).…”

“…ArOCCU ---> ArOCOOAr 1,2-Dichloro-l,2,2-tribromoethyl ethyl ether was converted by moist air to oxalic acid (360). Diehloromethyl trichloromethyl ether was insoluble in cold water; heated with water, it hydrolyzed slowly to carbon monoxide, carbon dioxide, hydrogen chloride, hexachloroethane, and other products (311).…”

“…Thus 1-chlorovinyl ethyl ether gives ethyl acetate, in a violent reaction (99). CH2=CC10C2H6 + HOH -> CH3COOC2H6 + HC1 Imbert (187,190) and Crompton and others (75,76,360) described the preparation of chloroacetate or dichloroacetate esters from 1,2-dichlorovinyl or trichlorovinyl ethers, respectively.…”

“…CHClBrCClBrOC2H6 -» CClBr=CC10C2H6 (360) Dehydrohalogenation may be accomplished in other positions in the molecule of a polyhaloalkyl ether, if it is impossible for the -halogen atom to be involved.…”