The correct title of this article is 9-Borabicyclo[3.3.1]nonane. The substitution of any brackets is due to technical restrictions.
9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroborationreagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates.[1] 9-BBN is also known by its nickname 'banana borane'.[2] This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.[3][better source needed]
Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aqueous KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.
^Brown, H. C. (1975). Organic Syntheses via Boranes. New York: John Wiley & Sons. ISBN0-471-11280-1.
^Stix, Gary. "The Straight Dope: A Q&A with the Prof behind the Good Science in Breaking Bad". Scientific American Blog Network. Nature America, Inc. Retrieved 18 June 2017.
^"Molecules with Silly or Unusual Names - page 3". Chm.bris.ac.uk. 2014-05-07. Retrieved 2016-06-01.
^Soderquist, John A.; Brown, Herbert C. (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.
^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". Organic Syntheses.; Collective Volume, vol. 9, p. 107
^Balog, A.; Meng, D.; Kamenecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J.; Danishefsky, S. J. (1996). "Total Synthesis of (−)-Epothilone A". Angew. Chem. Int. Ed. Engl.35 (2324): 2801. doi:10.1002/anie.199628011.
^Liu, J.; Lotesta, S. D.; Sorensen, E. J. (2011). "A concise synthesis of the molecular framework of pleuromutilin". Chem. Commun. 47 (5): 1500–1502. doi:10.1039/C0CC04077K. PMC3156455. PMID 21079876.
December 18, 2023
borabicyclo, nonane, correct, title, this, article, borabicyclo, nonane, substitution, brackets, technical, restrictions, borabicyclo, nonane, organoborane, compound, this, colourless, solid, used, organic, chemistry, hydroboration, reagent, compound, exists, . The correct title of this article is 9 Borabicyclo 3 3 1 nonane The substitution of any brackets is due to technical restrictions 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 also known by its nickname banana borane 2 This is because rather than drawing out the full structure chemists often simply draw a banana shape with the bridging boron 3 better source needed 9 Borabicyclo 3 3 1 nonane NamesIUPAC name 9 Borabicyclo 3 3 1 nonaneOther names BorabicyclononaneBanana boraneIdentifiersCAS Number 280 64 8 N3D model JSmol Interactive imageAbbreviations 9 BBNChemSpider 71299 YECHA InfoCard 100 005 456EC Number 206 000 9PubChem CID 6327450UNII 4K4J8L1OG9CompTox Dashboard EPA DTXSID3074781InChI InChI 1S C8H15B c1 3 7 5 2 6 8 4 1 9 7 h7 9H 1 6H2 YKey FEJUGLKDZJDVFY UHFFFAOYSA N YInChI 1 C8H15B c1 3 7 5 2 6 8 4 1 9 7 h7 9H 1 6H2Key FEJUGLKDZJDVFY UHFFFAOYAESMILES B1 H 3 C2CCCC1CCC2 H B34C2CCCC4CCC2PropertiesChemical formula C 16H 30B 2Molar mass 244 04 g mol 1Density 0 894 g cm3Melting point 153 to 155 C 307 to 311 F 426 to 428 K Solubility in water ReactsHazardsGHS labelling PictogramsSignal word WarningHazard statements H250 H260 H314Precautionary statements P210 P222 P223 P231 P232 P260 P264 P280 P301 P330 P331 P302 P334 P303 P361 P353 P304 P340 P305 P351 P338 P310 P321 P335 P334 P363 P370 P378 P402 P404 P405 P422 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesPreparation edit9 BBN is prepared by the reaction of 1 5 cyclooctadiene and borane usually in ethereal solvents for example 4 5 nbsp The compound is commercially available as a solution in tetrahydrofuran and as a solid 9 BBN is especially useful in Suzuki reactions 6 7 8 Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aqueous KOH The steric demand of 9 BBN greatly suppresses the formation of the 2 substituted isomer compared to the use of borane See also editOrganoboron chemistry BoronReferences edit Brown H C 1975 Organic Syntheses via Boranes New York John Wiley amp Sons ISBN 0 471 11280 1 Stix Gary The Straight Dope A Q amp A with the Prof behind the Good Science in Breaking Bad Scientific American Blog Network Nature America Inc Retrieved 18 June 2017 Molecules with Silly or Unusual Names page 3 Chm bris ac uk 2014 05 07 Retrieved 2016 06 01 Soderquist John A Brown Herbert C 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 Soderquist John A Alvin Negron 1982 9 Borabicyclo 3 3 1 nonane Dimer Organic Syntheses 70 169 doi 10 15227 orgsyn 070 0169 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 Organic Syntheses Collective Volume vol 9 p 107 Balog A Meng D Kamenecka T Bertinato P Su D S Sorensen E J Danishefsky S J 1996 Total Synthesis of Epothilone A Angew Chem Int Ed Engl 35 2324 2801 doi 10 1002 anie 199628011 Liu J Lotesta S D Sorensen E J 2011 A concise synthesis of the molecular framework of pleuromutilin Chem Commun 47 5 1500 1502 doi 10 1039 C0CC04077K PMC 3156455 PMID 21079876 Retrieved from https en wikipedia org w index php title 9 Borabicyclo 3 3 1 nonane amp oldid 1183618443, wikipedia, wiki, book, books, library,
