A New Zincate‐Mediated Rearrangement Reaction of 2‐(1‐Hydroxyalkyl)‐1‐alkylcyclopropanol |
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| Authors: | Kenichi Nomura Seijiro Matsubara Prof. |
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| Affiliation: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku‐katsura, Nishikyo‐ku, Kyoto 615‐8510 (Japan), Fax: (+81)?75‐383‐2463 |
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| Abstract: | A novel rearrangement of 2‐(1‐hydroxyalkyl)‐1‐alkylcyclopropanol has been found. It proceeds in the presence of a catalytic amount of organozinc ate complex to give vic‐diols. The rearrangement can be applied to various types of 2‐(1‐hydroxyalkyl)‐1‐alkylcyclopropanol, which can be easily prepared from the corresponding α,β‐epoxyketones and bis(iodozincio)methane. When bicyclo[13.1.0]pentadecane‐1,15‐diol was treated with the organozinc ate complex, the corresponding 14‐membered cyclic vic‐diol was obtained. Thus, this rearrangement is also useful for changing the ring size of cyclic substrates. |
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| Keywords: | cyclopropanol homogeneous catalysis organozinc ate complexes rearrangement zinc |
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