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Borane–tetrahydrofuran : ウィキペディア英語版
Borane–tetrahydrofuran

Borane–tetrahydrofuran is a dipolar bond complex composed of borane and tetrahydrofuran (THF). These solutions are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds.〔Marek Zaidlewicz, Herbert C. Brown, Santhosh F. Neelamkavil, "Borane–Tetrahydrofuran" Encyclopedia of Reagents for Organic Synthesis, 2008 John Wiley & Sons. 〕
==Preparation and uses==
The complex is commercially available but can also be generated by the dissolution of diborane in THF. A practical route to this is the oxidation of sodium borohydride with iodine in THF.
The complex can reduce carboxylic acids to alcohols and is a common route for the reduction of amino acids to amino alcohols (e.g. valinol). It adds across alkenes to give organoboron compounds that are useful intermediates.〔George W. Kabalka, John T. Maddox, Timothy Shoup, and Karla R. Bowers "A Simple And Convenient Method For The Oxidation Of Organoboranes Using Sodium Perborate: (+)-isopinocampheol" Org. Synth. 1996, vol. 73, p. 116. 〕 The following organoboron reagents are prepared from borane-THF: 9-borabicyclo()nonane, Alpine borane, diisopinocampheylborane. It is also used as a source of borane (BH3) for the formation of adducts.〔Karen V. L. Crépy and Tsuneo Imamoto "Preparation Of (S,S)-1,2-Bis-(tert-butylmethylphosphino)ethane ((s,s)-t-Bu-bisp
*) As A Rhodium Complex" Org. Synth. 2005, vol. 82, 22. 〕

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