α‐Halogenäther, 41 [1] Zur Existenz von Chloräthylenoxid

Abstract

Durch Chlorierung von Äthylenoxid in flüssiger und in Dampfphase konnte Monochloräthylenoxid 1 als eine bei 65–67° siedende, wenig stabile Flüssigkeit erhalten werden. Die Struktur konnte auf physikalischem und chemischem Wege eindeutig sichergestellt werden.

Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde

“…Conversion of 2-Chloroethylene Oxide to 2-Chloroacetaldehyde and Glycolaldehyde. 2-Chloroethylene oxide has been reported to rearrange to 2-chloroacetaldehyde (Gross & Freiberg, 1969). This epoxide was synthesized and added to aqueous buffer; rearrangement to 2-chloroacetaldehyde was detected by using GC.…”

Mutation induction in chinese hamster V79 cells by two vinyl chloride metabolites, chloroethylene oxide and 2‐chloroacetaldehyde

“…The mutagenic activity of chloroethylene oxide and its rearrangement product 2-chloroacetaldehyde ( Gross and Freiberg, 1969;Zief and Schramm, 1964) was assayed in Chinese hamster V79 cells. Mutation frequency was scored with two different genetic markers either by resistance to 8-azaguanine (Chu and Malling, 1968) or by resistance to the steroidal compound ouabain (Baker er al., 1974).…”

“…As is evident from Table I, chloroethylene oxide caused a mutagenic response with a much lower toxicity as compared to that of 2-chloroacetaldehyde at equimolar concentration; the same result was obtained with microbial indicators . Thus, 2-chloroethylene oxide acts as a mutagen per se and not exclusively via its spontaneous rearrangement product 2-chloroacetaldehyde (Gross and Freiberg, 1969;Zieff and Schramm, 1964). The strong mutagenicity of these two compounds, as compared to that of 2-chloroethanol and monochloroacetic acid, points to a possible role for chloroethylene oxide and 2-chloroacetaldehyde in vinyl chloride carcinogenesis, since it is now recognized that the majority of chemical carcinogens, some of which cause cancer in man, have been found to be mutagens when tested as their ultimate reactive forms or when the parent compounds were combined with an in vitro or in vivo metabolic activation system (Miller and Miller, 1971 ;Huberman and Sachs, 1974).…”

“…Chloroethylene oxide (b.p., 65-67' C) was prepared by chlorination of ethylene oxide in the gas phase (Gross and Freiberg, 1969) Bio-transformation of vinyl chloride (I) to chloroethylene oxide UI), which rearranges to 2-chloroacetaldehyde (111). The latter is further oxidized to monochloroacetic acid (IV), a urinary metabolite in humans and rats following their exposure to vinyl chloride.…”

Metabolism and mutagenicity of halogenated olefins--a comparison of structure and activity.

“…4) reveals that the common feature of those which are mutagenic is an unsymmetric chlorine substitution, whereas the inactive compounds are characterized by a symmetric distribution of the chlorine atoms. There is evidence from the chemical literature that unsymmetric chlorine substitution renders the epoxides unstable (10,16), as compared to symmetric substitution, where the epoxides are relatively stable (17,18). The reason for the instability of an unsymmetric substituted oxirane is the preponderance of the electron withdrawal effect of the chlorine atom(s).…”