|
|Section2= |Section7= }} 9-Borabicyclo()nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration reagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates.〔Brown, H. C. “Organic Syntheses via Boranes” John Wiley & Sons, Inc. New York: 1975. ISBN 0-471-11280-1.〕 == Preparation == 9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example: : The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.〔 (a)(b) A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E.J. Sorensen and S.J. Danishefsky, "Total Synthesis of (–)-Epothilone A" Angew. Chem., Int. Ed. Engl., 1996, 35, 2801. (c) J. Liu, S. D. Lotesta and E. J. Sorensen, "A concise synthesis of the molecular framework of pleuromutilin", Chem. Commun., 2011, 47, 1500. 〕 Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aqueous KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「9-Borabicyclo(3.3.1)nonane」の詳細全文を読む スポンサード リンク
|