First isolation and characterization of an anti-apicophilic spirophosphorane bearing an oxaphosphetane ring: a model for the possible reactive intermediate in the Wittig reaction |
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Authors: | Kojima Satoshi Sugino Masaya Matsukawa Shiro Nakamoto Masaaki Akiba Kin-ya |
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Affiliation: | Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan. |
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Abstract: | An anti-apicophilic phosphorane bearing an oxaphosphetane ring, in which the ring carbon is apical and the ring oxygen is equatorial (C-apical), has been prepared as a thermally less stable stereoisomer of a phosphorane with an ordinary equatorial carbon-apical oxygen array in the oxaphosphetane ring (O-apical). This novel C-apical phosphorane, which could be considered to be a model compound of the reactive intermediate in the Wittig reaction, was fully characterized by NMR and X-ray structural analysis. The compound was found to easily isomerize to its more stable O-apical isomer, especially in the presence of proton sources, and the latter O-apical compound was found to furnish olefin at elevated temperatures. |
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