Oxidation with hydrogen peroxide leads to alcohols: Sterically demanding boranes offer enhanced selectivity. One example of a sterically demanding borane (9-BBN) is generated by the double addition of borane to 1,5-cyclooctadiene: 9-Borabicyclo [3.3.1]nonane.

Brown Hydroboration（布朗硼氢化）反应，是硼烷对烯烃进行协同顺式加成得到有机硼加成产物，然后在碱性条件下氧化得到醇的反应。 1956 年，美国普渡大学的布朗 (Herbert C. Brown) 教授首先报道发现了该反应。 在后来的几十年中， Brown 又对该反应进行了系统的研究，揭示了该反应的机理、区域选择性、立体选择性以及在有机合成中的许多重要应用。 所以，现在人们称该类反应为 Brown 硼氢化反应 。 Addition of boranes to alkenes. 图片来源：摩熵化学（MolAid） …

2019年8月12日 · An especially selective hydroborating reagent is prepared from 1,5-cyclooctadiene and borane. The product is a bicyclic compound of structure \(1\) (often abbreviated as 9-BBN), in which the residual \(\ce{B-H}\) bond adds to unhindered alkenes with much greater selectivity than is observed with other hydroborating reagents.

9-Borabicyclo [3.3.1]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. [1] 9-BBN is also known by its nickname 'banana borane'. [2] .

2017年11月20日 · Disiamylborane (Sia 2 BH) and 9-borabicyclo[3.3.1]nonane (9-BBN) are two common reagents for this hydroboration reaction. The oxidation reagents (a basic hydrogen peroxide solution) are the same for both alkenes and alkynes.

2017年5月24日 · 硼烷对烯烃进行协同顺式加成得到有机硼加成产物，然后在碱性条件下氧化得到醇的反应。 其特点是：（1）反应过程不发生重排；（2）反应为顺式加成；（3）与不对称烯烃加成时，符合反马尔可夫尼可夫规则。 有机硼烷可以发生多种反应，是一个多能的中间体，可以用来合成多种类型的有机化合物。 例如：烯烃的硼氢化-氧化反应可以制备醇；炔烃的硼氢化-氧化可以制备醛和酮，用其他有机试剂替代过氧化氢也可用于制备胺、卤代烷等。 反应机理. 反应实例. …

The 9-BBN has been elegantly employed for the convenient synthesis of the sixmembered ring boracyclane, borinane. Boracyclanes (Chart 17.1) like borinane ( 1 ), 3,5-dimethyl-borinane ( 2 ), and 3,6-dimethyl borepane ( 3 ) [1] are found to be advantageous hydroborating agents over 9-BBN in certain reactions involving free radical mechanism as ...

1977年5月24日 · Treatment of B-allyl-9-BBN with water leads to the formation of propene and B-hydroxy- 9-BBN which was identified by comparison of its 'H NMR spectrum (S 5.58, 1H; 1.8, -K 2H; 1.17 ppm, -2H) and "B NMR spectrfim (6 -56.6 ppm) with those of authentic samples prepared by treatment of 9-BBN with water.

9-Borabicyclo [3.3.1]nonane, a commercially available reagent, is the most versatile hydroborating reagent to synthesize organoboranes (B-R-9-BBN). The reagent exhibits remarkable regio-, chemo-, and stereoselectivity during hydroboration reactions. The organoboranes can be converted to C-H, C-O, C-N, C-S, C-halogen, C-metal and above all C-C ...

9-硼双环[3.3.1]壬烷 溶液 0.5 M in THF; CAS Number: 280-64-8; Synonyms: 9-BBN at Sigma-Aldrich