Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.