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Synlett 1996; 1996(7): 600-608
DOI: 10.1055/s-1996-5540
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Synthesis and Reactions of the Intermediates of the Wittig, Peterson, and their Related Reactions

T. Kawashima* , R. Okazaki1
  • *Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113, Japan, Fax +81-3-5800-6899; E-Mail takayuki@chem.s.u-tokyo.ac.jp
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Publication Date:
31 December 2000 (online)

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The title intermediates containing a tetracoordinate B atom, pentacoordinate Si, Ge, Sn, and P atoms, and tetracoordinate S and Se atoms, were successfully synthesized as stable compounds. The X-ray crystallographic analyses of Si, Ge, P, S, and Se compounds indicated that they have a distorted trigonal bipyramidal structure with two oxygen atoms at the apical positions, but those of B, Sn, and another type of Ge compounds demonstrated that they have a very distorted tetrahedral boron, a nearly square pyramidal tin, and a tetrahedral germanium interacting with an oxido anion, respectively. On heating all compounds containing group 13, 14, and 15 elements underwent the Wittig-type reaction to give the corresponding olefin. It was suggested that a tetracoordinate 1,2λ4-oxathietane is an intermediate of the Corey-Chaykovsky reaction.

The Wittig reaction - Peterson-type reactions - reaction intermediates - X-ray crystallographic analysis - highly coordinate compounds