Studies on Synthetic Pyrethroids

Part VIII. Addition of Ethyl Diazoacetate to Methyl α, β, δ-Trimethylsorbate

Abstract

Ethyl diazoacetate adds predominantly to the γδ-ethylenic bond of methyl α, β, δ-trimethylsorbate to yield the cyclopropane derivatives, which are shown by the isolation of (±)-cis-, and (±)-traps-caronic acids from ozonolysis and subsequent hypobromite oxidation of the adducts. One of the adduct acid, obtained crystalline m. p. 164-5°, is shown to be (±)-cis-3-(1'-methyl-2'-carboxypropenyl)-2, 2-dimethylcyclopropane-l-carboxylic acid both by spectroscopic and degrative evidence.