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Paper | Special issue | Vol 73, No. 1, 2007, pp.805-824
Published online, 7th September, 2007
DOI: 10.3987/COM-07-S(U)61
Some Reactions of O-Equatorial Spirophosphoranes Bearing the Bidentate Ligand Based on Decafluoro-3-phenyl-3-pentanol

Xin-Dong Jiang, Shiro Matsukawa, Hideaki Yamamichi, and Yohsuke Yamamoto*

*Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-hiroshima 739-8526, Japan

Abstract

Some reactions of O-equatorial and O-apical methylphosphoranes bearing two bidentate ligands consisted of 1,1,1,2,2,4,4,5,5,5-decafluoro- 3-phenyl-3-pentanol were examined. Not only the O-apical phosphorane, but also the O-equatorial isomer did not react with MeLi as a nucleophile at the phosphorus center. This should be due to the steric bulkiness of the C2F5 group. For both isomers, deprotonation at the methyl group was achieved using Superbase (t-BuOK/n-BuLi) to give the corresponding α-anion, which was treated with several electrophiles to afford new phosphorane derivatives. The O-equatorial and O-apical phosphoranes having a β-hydroxyethyl group as the monodentate ligand were synthesized. It was found that under basic conditions, the O-apical phosphorane could be converted into the O-equatorial isomer via hexacoordinate phosphate intermediates.