9-Borabicyclo(3.3.1)nonane

The correct title of this article is 9-Borabicyclo[3.3.1]nonane. The substitution or omission of any < > [ ] { } is due to technical restrictions.
9-Borabicyclo(3.3.1)nonane
IUPAC name

9-Borabicyclo[3.3.1]nonane
Other names

Borabicyclononane
Identifiers
Abbreviations 9-BBN
CAS number 280-64-8 Y
PubChem 24855264
ChemSpider 71299 Y
EC number 206-000-9
Jmol-3D images Image 1
Properties
Molecular formula C16H30B2
Molar mass 244.03 g mol−1
Density 0.894 g/cm3
Melting point

153-155 °C, 426-428 K, 307-311 °F
Solubility in water Reacts
Hazards
R-phrases R11 R14/15 R36/37/38
S-phrases S7/9 S16 S33 S7/8 S26 S37/39
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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] Like other organoboron compounds, 9-BBN is pyrophoric.

Preparation

9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example:[2][3]

The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.[4]

Its highly stereoselective addition on olefins allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aq. KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.

References

  1. ^ Brown, H. C. “Organic Syntheses via Boranes” John Wiley & Sons, Inc. New York: 1975. ISBN 0-471-11280-1.
  2. ^ John A. Soderquist, Herbert C. Brown (1981). "Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer". J. Org. Chem. 46 (22): 4599–4600. doi:10.1021/jo00335a067. 
  3. ^ John A. Soderquist and Alvin Negron (1998), "9-Borabicyclo[3.3.1]nonane Dimer", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0095 ; Coll. Vol. 9: 95 
  4. ^ (a)Tatsuo Ishiyama, Norio Miyaura, and Akira Suzuki, "Palladium(0)-catalyzed reaction of 9-alkyl-9-borabicyclo[3.3.1]nonane with 1-bromo-1-phenylthioethene: 4-(3-cyclohexenyl)-2-phenylthio-1-butene ", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0107 ; Coll. Vol. 9: 107 (b) A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E.J. Sorensen and S.J. Danishefsky, "Total Synthesis of (–)-Epothilone A" Angew. Chem., Int. Ed. Engl., 1996, 35, 2801. doi:10.1002/anie.199628011 (c) J. Liu, S. D. Lotesta and E. J. Sorensen, "A concise synthesis of the molecular framework of pleuromutilin", Chem. Commun., 2011, 47, 1500. doi:10.1039/C0CC04077K

External links