Borane → 1-Octene

HRID 374664Notes

Reaction equation

HRID 374664 reaction equation
[BH3:1].B#B.O1[CH2:8][CH2:7][CH2:6][CH2:5]1>>[CH2:5]=[CH:6][CH2:7][CH2:8][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:5]([B:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:6][CH2:7][CH2:8][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6331Borane2×HCID 8028TetrahydrofuranHCID 6328200Diboron2×

Product 2

HCID 81251-OcteneHCID 11142667Trioctylborane

Procedure

In the practice of the invention, borane adducts of N,N-diisopropylalkylamines are prepared by passing diborane into a neat amine until no more diborane is absorbed. The adduct with N,N-diisopropylisobutylamine is liquid above 0° C., 4.6M in borane, and is stable over prolonged periods at room temperature. The adduct with N,N-diisopropyl-sec-butylamine is a liquid 3.3M in borane when freshly prepared at 0° C., slowly losing borane at room temperature. All of the adducts of this invention hydroborate 1-octene in tetrahydrofuran at room temperature in less than 1 hour to give trioctylborane. They are also soluble in diethyl ether and dichloromethane. Alternatively, neat adducts can be used for hydroboration.

Workup

  1. customis absorbed
  2. customliquid above 0° C., 4.6M in borane
  3. waitover prolonged periods at room temperature
  4. customfreshly prepared at 0° C.
  5. customat room temperature

Sources & evidence

ORD record
ord-c20380f3143c4eeb803404dc60b4e7d9
Source dataset
uspto-grants-1996_01
Patent number
US05481038

Reaction notes

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