Synthesis of Halomethylvinylcyclopropanecarboxylic Acids and Their Esters

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The 3-(2-halo- 1 -propenyl)-2, 2-dimethylcyclopropanecarboxylates were synthesized. They have four diastereoisomers: E/Z and cis/trans configurations with respect to the 2-halo-1-propenyl side chain and to the cyclopropane ring, respectively. The 3-(2-Chloro-l-propenyl)-2, 2-dimethylcyclopropane carboxylates were prepared via ethyl 3, 3-dimethyl-4, 6, 6-trichloroheptanoate (2) as a key intermediate and the 2-bromo- l-propenyl derivatives were obtained by the Wittig reaction. The stereochemistry of each of the four diastereoisomers was examined by 1H NMR spectroscopy.
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