Misplaced Pages

Alpine borane: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editNext edit →Content deleted Content addedVisualWikitext
Revision as of 11:23, 29 November 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Revision as of 09:43, 9 March 2011 edit undoColmere (talk | contribs)44 editsmNo edit summaryNext edit →
Line 39: Line 39:
}} }}


'''Alpine borane''' is the commercial name for an ] that is used in ]. This ] is generated by treating ] with ] to give a sterically crowded trialkylborane. The resulting ] species ]ly reduces deutero aldehydes:<ref>M. Mark Midland "B-3-Pinanyl-9-borabicyclononane" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley, New York.{{DOI|10.1002/047084289X.rp173}}. Article Online Posting Date: April 15, 2001</ref> '''Alpine borane''' is the commercial name for an ] that is used in ]. This ] is generated by treating ] with ] to give a sterically crowded trialkylborane. The resulting ] species can ]ly reduce ketones, aldehydes, even deutero aldehydes in what is known as the ], or simply the '''Midland Reduction''':<ref>M. Mark Midland "B-3-Pinanyl-9-borabicyclononane" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley, New York.{{DOI|10.1002/047084289X.rp173}}. Article Online Posting Date: April 15, 2001</ref>
:C<sub>8</sub>H<sub>12</sub>B-pinanyl + RCDO → C<sub>8</sub>H<sub>12</sub>BOCHDR + (+)-''d''-pinene :C<sub>8</sub>H<sub>12</sub>B-pinanyl + RCDO → C<sub>8</sub>H<sub>12</sub>BOCHDR + (+)-''d''-pinene


Revision as of 09:43, 9 March 2011

Alpine borane
Names
IUPAC name 9-(2,6,6-Trimethylbicyclohept-3-yl)-9-bora-bicyclononane
Other names Alpine-Borane; B-Isopinocampheyl-9-borabicyclononane; B-3-Pinanyl-9-borabicyclononane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.575 Edit this at Wikidata
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1Key: VCDGSBJCRYTLNU-AZWGFFAPSA-N
  • InChI=1/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1Key: VCDGSBJCRYTLNU-AZWGFFAPBY
SMILES
  • CC4(C)1C4(C)(C1)B3C2CCCC3CCC2
Properties
Chemical formula C18H31B
Molar mass 258.26 g·mol
Appearance Colorless liquid
Density 0.947 g/mL
Boiling point >55 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. This reagent is generated by treating 9-BBN with α-pinene to give a sterically crowded trialkylborane. The resulting chiral species can stereoselectively reduce ketones, aldehydes, even deutero aldehydes in what is known as the Midland Alpine Borane Reduction, or simply the Midland Reduction:

C8H12B-pinanyl + RCDO → C8H12BOCHDR + (+)-d-pinene

Hydrolysis of the resulting borinic ester affords the alcohol:

C8H12BOCHDR + H2O → C8H12BOH + HOCHDR

It is also effective for the stereoselective reduction of certain acetylenic ketones.

Related reagents

A range of alkyl-substituted derivatives of borane and diborane are specialty reagents in organic synthesis. Two such reagents that are closely related to Alpine borane are 9-BBN and diisopinocampheylborane.

References

  1. R-Alpine-Borane and S-Alpine-Borane at Sigma-Aldrich
  2. M. Mark Midland "B-3-Pinanyl-9-borabicyclononane" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley, New York.doi:10.1002/047084289X.rp173. Article Online Posting Date: April 15, 2001
  3. M. Mark Midland and Richard S. Graham. "Asymmetric Reduction of α,β-Acetylenic Ketones with B-3-Pinanyl-9-Borabicyclo[3.3.1]nonane: (R)-(+)-1-Octyln-3-ol". Organic Syntheses; Collected Volumes, vol. 7, p. 402.
Categories: