Key result
The CHI3–Et2Zn system is a convenient route for iodocyclopropanes, producing yields of 34% to 70% depending on the olefin used.
The CHI3–Et2Zn system provides a convenient route for the iodocyclopropanation of olefins.
The CHI3–Et2Zn system offers a viable iodocyclopropanation route; leaves open optimization for broader scope and higher yields.
The iodocyclopropanation of olefins by the iodocarbenoid of zinc generated from diethylzinc and iodoform was investigated. When the reaction was carried out in a neat olefin, cyclohexene, 1-hexene, cis-2-butene, isobutene, and styrene gave the corresponding iodocyclopropanes in yields of 70, 34, 63, 55, and 44% respectively, showing that the CHI3–Et2Zn system is a convenient route for iodocyclopropanes. The reaction with cyclohexene was investigated in some detail. syn-7-Iodonorcarane easily gave 3-ethylcycloheptene upon treatment with diethyl zinc in the presence of zinc iodide.
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Miyano et al. (1974) studied this question. Iodocyclopropanation of olefins with diethylzinc and iodoform was evaluated on Yield of iodocyclopropanes. The CHI3–Et2Zn system is a convenient route for iodocyclopropanes, producing yields of 34% to 70% depending on the olefin used.
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