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catecholborane : ウィキペディア英語版
catecholborane

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Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH.
==Synthesis and structure==
Traditionally catecholborane is produced by treating catechol with borane (BH3) in a cooled solution of THF. However, this method results in a loss of 2 mole equivalents of the hydride. Nöth and Männig devised a more economical method involves the reaction of alkali-metal boron hydride (LiBH4, NaBH4, of KBH4) with tris(catecholato)bisborane in an ethereal solvent such as diethyl ether.〔(Process for producing catecholborane - Patent 4739096 )〕 In 2001 Herbert Brown released an additional procedure for catecholborane synthesis. His method involves treating tri-''O''-phenylene bis-borate with diborane in a solution of either triglyme or tetraglyme. Brown claimed his method produces 85% yield of 97% pure product, catecholborane.〔(New Economical, Convenient Procedures for the Synthesis of Catecholborane )〕
Unlike borane itself or alkylboranes, catechol borane exists as a monomer. This behavior is a consequence of the electronic influence of the alkoxy groups that diminish the Lewis acidity of the boron centre. Pinacolborane adopts a similar structure.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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