Difference between revisions of "9-Borabicyclononane"
Physchim62 (talk | contribs) |
Physchim62 (talk | contribs) |
||
| Line 87: | Line 87: | ||
'''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> Like other organoboron compounds, 9-BBN is [[pyrophoric]]. | '''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> Like other organoboron compounds, 9-BBN is [[pyrophoric]]. | ||
| − | 9-BBN is prepared by the reaction of [[1,5-cyclooctadiene]] and [[borane]] usually in etherial solvents.<ref>{{citation | title = Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo | + | 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 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]]. | 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 == | ||
| − | {{ | + | {{reflist}} |
== External links == | == External links == | ||
Revision as of 07:59, 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.
| 9-Borabicyclo[3.3.1]nonane | |
|---|---|
| IUPAC name | 9-Borabicyclo[3.3.1]nonane |
| Other names | Borabicyclononane |
| Identifiers | |
| Abbreviations | 9-BBN |
| InChI | InChI=1/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2 |
| InChIKey | AMKGKYQBASDDJB-UHFFFAOYAO |
| Standard InChI | InChI=1S/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2 |
| Standard InChIKey | AMKGKYQBASDDJB-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| SMILES | |
| Properties | |
| Chemical formula | C16H26B2 |
| Molar mass | 244.04 g/mol |
| Appearance | white solid |
| Density | 0.894 g/cm3 |
| Melting point |
153–155 °C |
| Solubility in water | reacts |
| Hazards | |
| EU index number | not listed |
| Related compounds | |
| Other compounds | 9-Borabicyclononane dimer |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 9-Borabicyclo[3.3.1]nonane dimer | |
|---|---|
 |
 |
| |
| Identifiers | |
| Abbreviations | 9-BBN |
| InChI | InChI=1/C16H30B2/c1-5-13-7-2-8-14(6-1)17(13)19-18(20-17)15-9-3-10-16(18)12-4-11-15/h13-16H,1-12H2 |
| InChIKey | QQDDHBYRUTZKSX-UHFFFAOYAH |
| Standard InChI | InChI=1S/C16H30B2/c1-5-13-7-2-8-14(6-1)17(13)19-18(20-17)15-9-3-10-16(18)12-4-11-15/h13-16H,1-12H2 |
| Standard InChIKey | QQDDHBYRUTZKSX-UHFFFAOYSA-N |
| CAS number | [] |
| ChemSpider | |
| SMILES | |
| Properties | |
| Chemical formula | C16H26B2 |
| Molar mass | 244.04 g/mol |
| Appearance | white solid |
| Density | 0.894 g/cm3 |
| Melting point |
153–155 °C |
| Solubility in water | reacts |
| Hazards | |
| EU index number | not listed |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
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.
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. 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
- ↑ 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
| Error creating thumbnail: Unable to save thumbnail to destination |  |
This page was originally imported from Wikipedia, specifically this version of the article "9-Borabicyclononane". Please see the history page on Wikipedia for the original authors. This WikiChem article may have been modified since it was imported. It is licensed under the Creative Commons Attribution–Share Alike 3.0 Unported license. |
