Reactions of group V organometalloidal compounds. Part VI. Ring opening of β-propiolactone and of epoxides with dialkylamino(dimethyl)-arsines

Abstract

Treatment of β-propiolactone with dialkylamino(dimethyl)arsines at 80° in benzene gave dimethylarsenic 3-dialkylaminopropionates, formed by alkyl–oxygen bond fission. The addition reactions of dialkylamino(dimethyl)arsines with 1,1,1-trichloro-2,3-epoxypropane took place with normal fission of the epoxide ring to give 2-dialkylamino-1-trichloromethylethoxy(dimethyl)arsines. Although 1-chloro-2,3-epoxypropane was less reactive than the trichloro-compound, its mode of ring opening was the same. Degradation of the products of these reactions showed that the nucleophilic site in the aminoarsines was the nitrogen, rather than the arsenic atom.