Disiamylborane

Disiamylborane
Skeletal formula of disiamylborane
Ball-and-stick model of the disiamylborane molecule
Names
IUPAC name
Bis(1,2-dimethylpropyl)borane
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C10H23B
Molar mass 154.09 g/mol
Melting point 35-40 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Disiamylborane (bis(1,2-dimethylpropyl)borane, Sia2BH) is an organoborane used in organic synthesis. It is used to add water to a terminal alkyne, forming an aldehyde via anti-Markovnikov addition. Disiamylborane is relatively selective for terminal alkynes. It also is used for the selective functionalization of terminal alkenes.[1] 9-Borabicyclo[3.3.1]nonane (9-BBN) is another reagent that can be used for these purposes. Disiamylborane can be selectively prepared from hydroboration trimethylethylene; the reaction stops at the secondary borane due to steric hindrance.

Naming

"Siamyl" is an abbreviation for sec-isoamyl. More modern conventions replace amyl with the pentyl group,[2] and dispense with the sec and iso naming of pentyl isomers in favor of systematic naming as a substituted alkyl chain.[3] A related reagent named thexylborane ((1,1,2-trimethylpropyl)borane, ThxBH2) is a primary borane obtained from hydroboration of the even more hindered tetramethylethylene. In this compound, "thexyl" is an abbreviation for tert-hexyl.

References

  1. ↑ Eric J. Leopold (1990). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol". Organic Syntheses. ; Collective Volume, 7, p. 258
  2. ↑ "Friday Dec 4 Lecture" (PDF). Amherst University.
  3. ↑ "Disiamylborane". PubChem.
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