ORGN 132 |
| 1-Alkynylphosphonates easily prepared by the deprotonation of the terminal alkynes with n-butyllithium followed by reaction with diethylchlorophosphonates, readily undergo dihydroboration with 9-borabicyclo[3.3.1]nonane (9-BBN) in tetrahydrofuran at room temperature for 12 hours. The resulting dihydroborated products are reacted with alkaline hydrogen peroxide at 0 oC followed by stirring at room temperature for 4 hours to provide the corresponding 1-alkanols containing alpha-phosphonate moiety in excellent yields (72%-84%). The structures of these hydroxyphosphonates are confirmed by PMR and CMR spectral data.
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Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |