Wheel of Diborane Reactions

The banana-bonded🍌 Diborane!


The mechanism of hydroboration oxidation (via Brown hydroboration or Brown-Subba Rao hydroboration, which is an addition of boranes to alkenes) is believed to be concerted and anti-Markovnikov’s product is usually formed (say, an alcohol by the 'net' addition of water). A good number of borane complexes (BH3•X), the monoalkylborane (RBH2), and dialkylborane (R2BH) reagents have been prepared. The reagent 9-BBN (9-Borabicyclo[3.3.1]nonane) is one of the most important ones.



Wheel of Brown hydroboration reactions: Click/tap to enlarge the image


Substrates (on the infographic):

  1. Cycloocta-1,5-diene (COD)
  2. 3-Methylbut-2-ene
  3. Dimethyl sulfide
  4. Triethylborane, H3B•Me2S
  5. α--Pinene, H3B•Me2S
  6. Cyclohexene, H3B•Me2S, H3B•THF
  7. Tetrahydrofuran
  8. 2,3-Dimethylbut-2-ene

What other wheel(s) 🎡 of organic reactions would you like to see ❓Questions❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗


Reference:

Valiulin, R. Organic Chemistry: 100 Must-Know Mechanisms; De Gruyter: Berlin, 2023.

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