Difference between revisions of "9-Borabicyclononane"
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| − | '''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.<ref>{{citation | last = Brown | first = H. C. | authorlink = Herbert C. Brown | title = Organic Syntheses via Boranes | publisher = Wiley | location = New York | year = 1975 | isbn = 0-471-11280-1}}.</ref> | + | '''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.<ref name="BrownBook">{{citation | last = Brown | first = H. C. | authorlink = Herbert C. Brown | title = Organic Syntheses via Boranes | publisher = Wiley | location = New York | year = 1975 | isbn = 0-471-11280-1}}.</ref> |
| − | 9-BBN is prepared by the reaction of [[1,5-cyclooctadiene]] and [[borane]] adducts, usually in etherial solvents.<ref name="BrownJOC">{{citation | title = Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer | first1 = John A. | last1 = Soderquist | first2 = Herbert C. |last2 = Brown | authorlink2 = Herbert C. Brown | journal = J. Org. Chem. | year = 1981 | volume = 46 | issue = 22 | pages = 4599–4600 | doi = 10.1021/jo00335a067}}.</ref><ref name="OrgSynthPrepn">{{OrgSynth | first1 = John A. | last1 = Soderquist | first2 = Alvin |last2 = Negron | title = 9-Borabicyclo[3.3.1]nonane Dimer | prep = cv9p0095 | year = 1992 | volume = 70 | pages = 169 | collvol = 9 | collvolpages = 95}}.</ref> The compound is commercially available as a solution in [[tetrahydrofuran]] and as a solid. | + | 9-BBN is prepared by the reaction of [[1,5-cyclooctadiene]] and [[borane]] adducts, usually in etherial solvents.<ref name="BrownJOC">{{citation | title = Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer | first1 = John A. | last1 = Soderquist | first2 = Herbert C. |last2 = Brown | authorlink2 = Herbert C. Brown | journal = J. Org. Chem. | year = 1981 | volume = 46 | issue = 22 | pages = 4599–4600 | doi = 10.1021/jo00335a067}}.</ref><ref name="OrgSynthPrepn">{{OrgSynth | first1 = John A. | last1 = Soderquist | first2 = Alvin |last2 = Negron | title = 9-Borabicyclo[3.3.1]nonane Dimer | prep = cv9p0095 | year = 1992 | volume = 70 | pages = 169 | collvol = 9 | collvolpages = 95}}.</ref> The compound is commercially available as a solution in [[tetrahydrofuran]] and as a solid. |
| − | Its highly stereoselective addition on olefins allows the preparation of terminal alcohols by subsequent oxidative cleavage with [[hydrogen peroxide]] in aqueous [[potassium hydroxide]]. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of [[borane]]. | + | The solid is a hydride-bridged dimer:<ref name="BrownBook"/> solutions in THF and other donor solvents contain monomeric adducts with a solvent molecule, eg 9-BBN·THF. |
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| + | 9-BBN is especially useful in [[Suzuki reaction]]s.<ref>{{OrgSynth | first1 = Tatsuo | last1 = Ishiyama | first2 = Norio | last2 = Miyaura | first3 = Akira | last3 = Suzuki | title = 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 | prep = cv9p0107 | year = 1993 | volume = 71 | pages = 89 | collvol = 9 | collvolpages = 107}}.</ref> Its highly stereoselective addition on olefins allows the preparation of terminal alcohols by subsequent oxidative cleavage with [[hydrogen peroxide]] in aqueous [[potassium hydroxide]]. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of [[borane]]. | ||
== References == | == References == | ||
Revision as of 08:11, 23 August 2009
- The correct title of this article is 9-Borabicyclo[3.3.1]nonane. The substitution or omission of any < > [ ] { } is due to technical restrictions.
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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 prepared by the reaction of 1,5-cyclooctadiene and borane adducts, usually in etherial solvents.[2][3] The compound is commercially available as a solution in tetrahydrofuran and as a solid.
The solid is a hydride-bridged dimer:[1] solutions in THF and other donor solvents contain monomeric adducts with a solvent molecule, eg 9-BBN·THF.
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 hydrogen peroxide in aqueous potassium hydroxide. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.
References
- ↑ 1.0 1.1 Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975. ISBN 0-471-11280-1.
- ↑ Soderquist, John A.; Brown, Herbert C. Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer. J. Org. Chem. 1981, 46 (22), 4599–4600. DOI: 10.1021/jo00335a067.
- ↑ Soderquist, John A.; Negron, Alvin 9-Borabicyclo[3.3.1]nonane Dimer. Org. Synth. 1992, 70, 169, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0095>; Coll. Vol., 9, 95.
- ↑ Ishiyama, Tatsuo; Miyaura, Norio; Suzuki, Akira 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. 1993, 71, 89, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0107>; Coll. Vol., 9, 107.
External links
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