Y. Nishizawa
1961
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Journal
Agricultural and biological chemistry
Abstract
Phosdrin is the most popular compound in this series and is widely used as insecticide. J. E. Casida3) separated geometrical isomers of these compounds by distillation and silicagel columnchromatography, and found that alpha isomer is the most active as an insecticide and anticholinesterase agent but the exact isomeric configuration of the alpha and beta isomers from these substituted-vinyl phosphoroates is yet uncertain. From these reports, the present author in 19574) tried to prepare the cyclic-phosdrin type compound which has only one configuration and could confirm its structures. Recently, J. E. Casida5) reported, however, the alkaline stability, anticholinesterase activity and toxicity of the same compound, namely phosphoroates containing carboethoxy-cycloalkenyl-group, which had been prepared by the present author in 1957, but Casida did not report the synthetic method, confirmation of its structure of these compounds. So, in the present paper, the chemical properties of these new compounds and its thionoanologus compounds are mainly reported. All the compounds were prepared by two methods, one of which was the reaction of O,O-dialkyl phosphorochloridates (II, Y=O) or phosphorochloridothioates (II, Y=S) with sodium enolates of ethyl cyclopentanon-2carboxylate6) or ethyl cyclohexanon-2-carboxylate7) in an anhydrous benzene solution