2-Chloroethylvinyl ether

Dibromo-2-(2-chlorojethoxyethane 640 g of bromine (4 mols) are added dropwise, with stirring, to 426 g (4 mols) of 2-chloroethylvinyl ether dissolved in 1,040 ml of chloroform maintained at -10 C. 

Aliphatic and benzylic ethers are degraded by hydroxylation of the a-methylene group followed by scission of the ether bond with the formation of an aldehyde and an alkanol (White et al. 1996 Kim and Engesser 2004). In contrast, the degradation of 2-chloroethylvinyl ether by Ancylobacter... 

One of the early syntheses of meperidine (75) starts with the double alkylation of phenylacetonitrile with the bischloro-ethyl amine, 72. The highly lachrimatory nature of this material led to the development of an alternate synthesis for the intermediate piperidine (73). Alkylation of phenylacetonitrile with two moles of 2-chloroethylvinyl ether leads to the intermediate (69). This is then hydrolyzed without prior isolation to the diol, 70. Treatment with thionyl chloride affords the corresponding dichloro compound (71). This last is then used to effect a bis alkylation on methylamine, in effect forming the piperidine (73) by cyclization at the opposite end from the original scheme. Saponification to the acid (74) followed by esterification with ethanol affords the widely used analgesic meperidine (75) substitution of isopropanol for ethanol in the esterification affords properidine (76). ... 

A number of other unsaturated electrophilic compounds were used by Milkovich 18 as deactivators for living polystyrene or living polydienes. A characterization of the macromonomers obtained showed that the reaction of the living polymer with compounds such as maleic anhydride, vinyl chloroacetate, or 2-chloroethylvinyl ether yields the following unsaturated chain ends (in some cases the addition of 1,1-diphenylethylene is necessary) ... 

SYNONYMS vinyl 2-chloroethyl ether, (2-chloroethoxy) ethene, 2 -chloroethyl ethenyl ether, 2-ehloroethylvinylether, 2-chloroethylvinyl ether, 2-Vinyloxyethyl chloride... 

The above illustrated crosslinking reactions of homopolymers, however, form elastomers with poor aging properties. Commercial acrylic rubbers are therefore copolymers of ethyl or butyl acrylate with small quantities of comonomers that carry special functional groups for crosslinking. Such comonomers are 2-chloroethylvinyl ether or vinyl chloroacetate, used in small quantities (about 5%). These copolymers crosslink through reactions with polyamines. 

The first successful (3-pinene LCP systems were reported by Lu et al. in 1997 [42-44], The best conditions involved the use of the HCl adduct of 2-chloroethylvinyl ether, isopropoxytitanium chloride [Ti(OiPr)Cl3] in the presence of tetra-n-butylammonium chloride [nBuNCl] in dichloromethane at —40°C to —78°C, viz. a system previously optimized for the LCP of st5rene [45]. The living character of this system was clearly demonstrated by the fact that Mn increased linearly with monomer conversion, even after several monomer additions [43]. 

ACM acrylic ester rubber (acrylic ester - 2-chloroethylvinyl ether - polymethylene)... 

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