A borane is a compound with the formula BxHy or a related anion. Many such boranes are known. Most common are those with 1 to ... Hybrids of boranes and hydrocarbons, the carboranes are also well developed. The development of the chemistry of boranes led to ... For example, reaction of a borane cluster with B2H6 (as a source of BH3) can lead to the formation of a conjuncto-borane ... 10B + 1n → (11B*) → 4He + 7Li + γ (2.4 Mev) Category:Boranes, containing all specific borane-compound articles Sara Rietti, ...
... or dehydrocoupling of amine-boranes is a chemical process in main group and organometallic ... 5 rather than the typically seen cyclic dimers from other amine-borane dehydrogenations. When catalyzing ammonia-borane ... Secondary amine-boranes dehydrogenate to form cyclic dimers, or monomeric aminoboranes in the case of more bulky groups on the ... Ammonia borane has attracted particular interest due to its high weight percent of hydrogen (19.6%). Dehydrogenation occurs in ...
Phosphine-boranes, with the formula R3−nHnPBH3, are adducts of organophosphines and borane. Borane(5) is the dihydrogen complex ... Borane dimethylsulfide which is more stable than borane-tetrahydrofuran may also be used. Hydroboration can be coupled with ... Borane ammoniate, which is produced by a displacement reaction of other borane adducts, eliminates elemental hydrogen on ... Solutions containing borane dimethylsulfide and borane-tetrahydrofuran are commercially available; in tetrahydrofuran a ...
... is the inorganic compound with the formula H3BCO. This colorless gas is the adduct of borane and carbon ... Borane carbonyl has an enthalpy of vaporization of 19.7 kJ/mol (4750 cal/mol). It has electronic state 1A1 and point group ... Borane carbonyl was discovered in 1937 by reacting diborane with excess carbon monoxide, with the equation: B2H6 + 2 CO ⇌ 2 ... The structure of the molecule of borane carbonyl is H3B−−C≡O+. The B−C≡O linkage is linear. The coordination geometry around ...
R-Alpine-Borane and S-Alpine-Borane at Sigma-Aldrich M. M. Midland (1989). "Asymmetric reductions with organoborane reagents". ... Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. It is a colorless liquid, ... A range of alkyl-substituted borane are specialty reagents in organic synthesis. Two such reagents that are closely related to ... sterically crowded chiral trialkylborane can stereoselectively reduce aldehydes in what is known as the Midland Alpine borane ...
... where the borane is often tris(pentafluorophenyl)borane Ammonia borane, related to phosphine-borane but with ammonia or amines ... Typically phosphine-boranes are produced by treating the parent phosphine with a source of borane: PR3−nHn + BH3 → R3−nHnPBH3 ... "Methyldiphenylphosphine-Borane and Dimethylphenylphosphine-Borane". Inorganic Syntheses. Inorganic Syntheses. Vol. 15. pp. 128- ... In chemistry, phosphine-boranes are organophosphorus compounds with the formula R3−nHnPBH3. They are Lewis acid-Lewis base ...
Ammonia borane Borane dimethylsulfide Borane tert-butylamine Marek Zaidlewicz, Herbert C. Brown, Santhosh F. Neelamkavil, " ... The use of borane-tetrahydrofuran has been displaced by borane-dimethylsulfide, which has a longer shelf life and effects ... Borane-tetrahydrofuran is an adduct derived from borane and tetrahydrofuran (THF). These solutions, which are colorless, are ... The following organoboron reagents are prepared from borane-THF: 9-borabicyclo[3.3.1]nonane, Alpine borane, ...
Phosphine-borane (R3P→BH3) borane dimethylsulfide (Me2S→BH3) borane-tetrahydrofuran (THF→BH3) Shore, S. G.; Boddeker, K. W. ( ... Borane trimethylamine (Me3N→BH3) Borane isopropylamine (iPrNH2→BH3) The first amine adduct of borane was derived from ... Ammonia borane is the main product when an adduct of borane is employed in place of diborane: BH3(THF) + NH3 → BH3NH3 + THF It ... Ammonia borane has been suggested as a storage medium for hydrogen, e.g. for when the gas is used to fuel motor vehicles. It ...
... (BMS) is a chemical compound with the chemical formula BH3·S(CH3)2. It is an adduct between borane ... The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher ... Boranes add to alkenes in an anti-Markovnikov fashion and allow conversion of alkynes to the corresponding cis-alkenes. BMS has ... Borane dimethylsulfide is flammable and reacts readily with water to produce a flammable gas. It also has an unpleasant smell. ...
... is a key reagent leading to the concept of frustrated Lewis pairs. The combination of BCF and ... Tris(pentafluorophenyl)borane, sometimes referred to as "BCF", is the chemical compound (C6F5)3B. It is a white, volatile solid ... Tris(pentafluorophenyl)borane is also capable of abstracting hydride to give [(C6F5)3BH]−, and it catalyzes hydrosilylation of ... Tris(pentafluorophenyl)borane is thermally stable at temperatures well over 200 °C, resistant to oxygen, and water-tolerant. ...
... is an amine borane complex derived from tert-butylamine and borane. It is a colorless solid. The ... Ammonia borane Nöth, Heinrich; Beyer, Hasso; Vetter, Hans-Joanchim (1964). "Beiträge zur Chemie des Bors, XXV. Bis(amin)- ... borane tert-butylamine can be used for selective reduction of certain functional groups including aldehydes, ketones, oximes, ... "Tert-Butylamine borane". pubchem.ncbi.nlm.nih.gov. NCBI. Retrieved 3 September 2019. (Articles without InChI source, Articles ...
The Alpine borane can be synthesized by refluxing alpha-pinene and 9-BBN in THF. While both enantiomers of alpine borane are ... The Midland Alpine borane reduction, or simply the Midland reduction, allows for the asymmetric reduction of carbonyls ( ... The stereochemical control comes from coordination of the bulky borane to the carbonyl, followed by hydride transfer opposite ...
In order to prevent hydroboration across both the pi-bonds, a bulky borane like disiamyl (di-sec-iso-amyl) borane is used. Use ... In the first step, borane (BH3) adds to the double bond, transferring one of the hydrogen atoms to the carbon adjacent to the ... Alkyl migration to oxygen gives the alkyl borane with retention of stereochemistry (in reality, the reaction occurs via the ... Hawthorne, M. F. (1961). "Amine Boranes. VIII. The Hydroboration of Terminal Olefins, Dienes and Terminal Acetylenes with ...
Among the geometric isomers, one with chirality was the first borane to be resolved into its separate enantiomers, and was only ... Octadecaborane is an inorganic compound, a borane with chemical formula B18H22. It is a colorless flammable solid, like many ... Heřmánek, S.; Plešek, J. (1970). "Chemistry of boranes. XXI. Resolution of iso-octadecaborane to optical enantiomers". ... This compound was the first borane found to have multiple isomeric forms. ...
This will strip off borane to combine with the Lewis base, and let two methyl borane molecules dimerise. Methyldiborane can ... and can be imagined as methyl borane (CH3BH2) bound to borane (BH3). Other combinations of methylation occur on diborane, ... As with other boranes it exists in the form of a dimer with a twin hydrogen bridge that uses three-center two-electron bonding ... A gas chromatograph can be used to determine the amounts of the methyl boranes in a mixture. The order they pass through are ...
9-BBN is also known by its nickname 'banana borane'. This is because rather than drawing out the full structure, chemists often ... The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane. ... Organoboron chemistry Boron Brown, H. C. (1975). Organic Syntheses via Boranes. New York: John Wiley & Sons. ISBN 0-471-11280-1 ... 5-cyclooctadiene and borane usually in ethereal solvents, for example: The compound is commercially available as a solution in ...
Brown, H. C. (1975). Organic Syntheses via Boranes. New York: John Wiley & Sons. ISBN 0-471-11280-1. Palladium hydride Züttel, ... borane, BH3 aluminium: alumane, AlH3 gallium: gallane, GaH3 indium: indigane, InH3 thallium: thallane, TlH3 carbon: alkanes, ... also borane, pentaborane and decaborane arsine: used for doping semiconductors stibine: used in semiconductor industry ...
Isadore Shapiro; C. O. Wilson; J. F. Ditter; W. J. Lehmann (1961). Borax to Boranes (PDF). Advances in Chemistry Series. Vol. ... More methylated boranes are less stable. 1,2-Dimethyldiborane slowly converts to 1,1-dimethyldiborane. Methylborane hydrolyzes ... By treating monomethyldiborane with ether, dimethyl ether borane (CH3)2O.BH3 leaving methylborane which rapidly dimerises to 1, ... by Borane: the Intimate Mechanism of an Alkyl Transfer Reaction". Journal of the American Chemical Society. 104 (9): 2361-2365 ...
"Borane". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-22. PubChem. "Borax". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-22. ... Bi2WO6 Borane - BH3 Borax - Na2B4O7·10H2O Borazine - B3H6N3 Borazocine ((3Z,5Z,7Z)-azaborocine) - B4H8N4 Boric acid - H3BO3 ...
Borane adducts with phosphines and amines are also available, but are not widely used. Borane makes a strong adduct with ... This significant rate difference in producing di- and tri-alkyl boranes is useful in the synthesis of bulky boranes that can ... See Borane-dimethylsulfide complex Zaidlewicz, Marek; Baum, Ofir; Srebnik, Morris (2006). "Borane Dimethyl Sulfide". ... More sterically hindered tertiary and silyl amines can deliver borane to alkenes at room temperature. Monoalkyl boranes are ...
The latter involved an extension of the Wade's Rules for polyhedral boranes to macropolyhedral boranes and the Huckel 4n+2 Rule ... The Jemmis mno rules for polyhedral boranes have found a place in textbooks and are being taught in Inorganic Chemistry Courses ... Shameema, O.; Jemmis E. D. (2008). "Orbital Compatibility in the Condensation of Polyhedral Boranes". Angew. Chem. Int. Ed. 47 ... Jemmis, E. D.; Balakrishnarajan M. M. (2001). "Polyhedral Boranes and Elemental Boron: Direct Structural Relations and Diverse ...
... the higher boranes and borane anions, and various transition-metal carbonyl cluster compounds". J. Chem. Soc. D. 1971 (15): 792 ... as is the case for many boranes and carboranes. For such clusters, the structures are based on deltahedra, which are polyhedra ... provides electron counting rules useful for predicting the structures of clusters such as borane and carborane clusters. The ... A Graph-Theoretical Interpretation of the Bonding Topology in Polyhedral Boranes, Carboranes, and Metal Clusters". J. Am. Chem ...
The Boranes and Their Relatives. in Les Prix Nobel en 1976. Imprimerie Royal PA Norstedt & Soner, Stockholm. 110-131.[1][2] ... The 1976 Nobel Prize in Chemistry was awarded to Lipscomb "for his studies on the structure of boranes illuminating problems of ... The diagram at right shows a typical nuclear magnetic resonance (NMR) spectrum of a borane molecule. Lipscomb investigated ... Lipscomb and his graduate students further determined the molecular structure of boranes (compounds of boron and hydrogen) ...
The Jemmis mno rule provides the relationship between polyhedral boranes, condensed polyhedral boranes, and β-rhombohedral ... the higher boranes and borane anions, and various transition-metal carbonyl cluster compounds". J. Chem. Soc. D (15): 792. doi: ... They were formulated by E. D. Jemmis to explain the structures of condensed polyhedral boranes such as B20H16, which are ... The Jemmis mno rules are an extension of Wade's rules, generalized to include condensed polyhedral boranes as well. The first ...
The dodecaborate(12) anion, [B12H12]2−, is a borane with an icosahedral arrangement of 12 boron atoms, with each boron atom ... Miller, H. C.; Muetterties, E. L.; Boone, J. L.; Garrett, P.; Hawthorne, M. F. (2007). "Borane Anions". Inorganic Syntheses. pp ... Boranes, Anions, Substances discovered in the 1960s). ...
Fullerene chemistry Carborane Boranes Hirsch, Andreas; Chen, Zhongfang; Jiao, Haijun (2000), "Spherical Aromaticity in Ih ... Spherical Aromaticity: Recent Work on Fullerenes, Polyhedral Boranes, and Related Structures (Aromatic compounds, Physical ... polyhedral boranes. In 2000, Andreas Hirsch and coworkers in Erlangen, Germany, formulated a rule to determine when a fullerene ...
Muetterties's work on boron hydride clusters led to the work on several polyhedral borane anions such as B12H122−. He was an ... In addition to the polyhedral boranes, the program explored pi-allyl, fluoroalkyl, and boron hydride complexes of the ... Journal of the American Chemical Society (1957), 79 3686-7. Hawthorne, M. Frederick (March 23, 2009). "Polyhedral Boranes: ... who is known for his experimental work with boranes, homogeneous catalysis, heterogeneous catalysis, fluxional processes in ...
Holthausen, Michael H.; Mallov, Ian; Stephan, Douglas W. (2014). "Phosphinimine-substituted boranes and borenium ions". Dalton ...
Atkins, William J. Jr.; Burkhardt, Elizabeth R.; Matos, Karl (2006). "Safe Handling of Boranes at Scale". Org. Process Res. Dev ...
... is the borane with the formula (CH3)4C2O2BH. Often pinacolborane is abbreviated HBpin. It features a boron ... Brown, H.C.; Zaidlewicz, M. (2001). Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. ISBN 978-0- ...