1.4- Dichloro-2,3-epoxybutane

Further, if there is a conformational change reflected by viscosity, we can expect that it will be reflected also in other macroscopic properties of the solution. Forsman and Poddar (12) have studied viscosity of stereoisomers of poly (1, 4-dichloro-2,3-epoxybutane) in a series of solvents dimethylformamide,... 

Fig. 10.25. Reaction pathway of butadiene monoxide (10.102) in aqueous NaCl solution to yield l,2-dichloro-3,4-epoxybutane (10.111) [168], The sequence involves the intermediate...

Solvolysis of butadiene monoxide (10.102) in saline solution is a rather unexpected reaction that further documents this compound s reactivity [168]. In aqueous NaCl solution at physiological pH and temperature, butadiene monoxide disappeared rapidly to form 1,2-dichloro-3,4-epoxybutane (10.111, Fig. 10.25). There was a linear dependence of the rate of reaction on the Cl concentration (in the range investigated (34-135 mM)). The reaction pathway was described as slow solvolytic formation of the bu-tenylchloronium ion, followed by Cl attack to yield Cl2 and butadiene. Cl2 is then rapidly trapped by a second molecule of butadiene monoxide to form a different chloronium ion that also reacts with Cl to yield the final, stable dichloro product (10.111). The formation of 1,2-dichloro-3,4-epoxy-butane under physiological conditions is believed to be toxicologically significant. 

Vogel, E. (1979) Mutagenicity of chloroprene, 1 -chloro-1,3-Zrazw-butadiene. 1,4-dichlorobutene-2 and l,4-dichloro-2,3-epoxybutane to. Drosophila melanogaster. Mutat. Res., 61, 377-381... 

---