A [2++4] polar cycloaddition of α-chlorosulfides with conjugated dienes: one-pot synthesis of 1-acyl- and 1-cyano-1-methylthio-2-vinylcyclopropanes |
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| Authors: | H Ishibashi Y Kitano H Nakatani M Okada M Ikeda M Okura Y Tamura |
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| Institution: | Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan;Faculty of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565, Japan |
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| Abstract: | In the presence of SnCl4, methoxycarbonyl-, acetyl-, benzoyl-, or cyano-substituted chloromethyl methyl sulfide (1–4) undergoes 2++4] polar cycloaddition with conjugated dienes to afford the cycloadducts of type 7, which, on treatment with base, are converted into the 1-acyl- or 1-cyano-1-methylthio-2-vinylcyclopropanes 9–10 via the ylide intermediates of type 8. |
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