16872-09-6Relevant articles and documents
Practical synthesis for decahydrodecaborates
Makhlouf, Joseph M.,Hough, William V.,Hefferan, Gerald T.
, p. 1196 - 1198 (1967)
High-yield synthesis of the decahydrodecaborate(2-) anion was achieved from the thermolysis of tetraethylammonium tetrahydroborate(1-), (C2H5)4NBH4, and tetraethylammonium octahydrotriborate(1-), (C2H5)4NB3H8, at atmospheric pressure and 185°. The thermolysis of tetramethylammonium tetrahydroborate(1-), (CH3)4NBH4, under similar conditions gives only trimethylamine borane, (CH3)3NBH3, and methane, while a near equimolar mixture of [(CH3)4N]2B10H10 and [(CH3)4N]2B12H12 was the major product obtained from pyrolysis of tetramethylammonium octahydrotriborate(1-), (CH3)4NB3H8. Although B10H102- was a major product, complex mixtures of products containing the BH4-, B10H102-, B11H14-, and B12H122- anions were obtained from the 185° pyrolysis of potassium and cesium octahydrotriborates(1-), KB3H8 and CsB3H8, respectively. No evidence was obtained for B9H92- or B11H112- when the pyrolysis temperatures were maintained at 185°.
Reduction of hydroxy-functionalised carbaboranyl carboxylic acids to tertiary alcohols by organolithium reagents
Neumann, Wilma,Hiller, Markus,Loennecke, Peter,Hey-Hawkins, Evamarie
, p. 4935 - 4937 (2014)
Reduction of hydroxy-functionalised carbaboranyl carboxylic acids by organolithium reagents yields the corresponding tertiary alcohols. This is in contrast to exo-polyhedral C-C bond cleavage of unsubstituted carbaboranyl carboxylic acids upon reaction with lithium organyls. The proposed dimeric contact ion pairs may also explain the formation of tertiary alcohols instead of the expected ketones.
A novel approach to ortho-carborane by decarboranylation of 1-(isopropyl benzoate)-1,2-dicarba-closo-dodecaborane
Feng, Chen,Zhang, Haicheng,Yang, Jiping,Chen, Gong
, p. 2027 - 2029 (2015)
Abstract A novel approach was successfully developed for the synthesis of ortho-carborane [1,2-dicarba-closo-dodecaborane(12)] by reaction of 1-(isopropyl benzoate)-1,2-dicarba-closo-dodecaborane with KOH in methanol at 20 C. A decarboranylation in base of the first formed alcoholysis intermediate product 1-(2-propanol)-1,2-dicarba-closo-dodecaborane was suggested for this process.
Access to carbaboranyl glycophosphonates - An odyssey
Stadlbauer, Sven,Welzel, Peter,Hey-Hawkins, Evamarie
, p. 5005 - 5010 (2009)
Novel bis-phosphonate derivatives of carbaboranes, which might be potential boron-delivery agents for boron neutron capture therapy, are described. Conceivable synthetic routes which failed to give the desired compounds are discussed, and finally, a highl
Carboranes. I. The preparation and chemistry of 1-isopropenylcarborane and its derivatives (a new family of stable clovoboranes)
Fein, Marvin M.,Bobinski, Jack,Mayes, Nathan,Schwartz, Nelson,Cohen, Murray S.
, p. 1111 - 1115 (1963)
The preparation of the first member of a new family of stable polycyclic boranes is reported. Treatment of isopropenyl-acetylene with derivatives of decaborane of the form B10H12·L2 (where L is any one of several Lewis bases) or with mixtures of decaborane and L give the new polycyclic borane. The general applicability of this reaction to other acetylenes is also reported. The cycloboranes which are formed contain a =C2B10H10 unit and are members of the generic family, C2BnHn+2. The nucleus exhibits a high degree of oxidative, hydrolytic, and thermal stability.
Carbon extrusion in 1,2-dicarba-closo-dodecaboranes: Regioselective boron substitution in ten-vertex closo-monocarbaborane anions
Laromaine, Anna,Teixidor, Francesc,Vinas, Clara
, p. 2220 - 2222 (2005)
(Chemical Equation Presented) A nonclassical carbon atom of a dicarbaborane is converted into a classical carbon atom, and the substituent increases in length by one CH2 group (see scheme). This is the path followed to form [1-Me-6-Et-1-closo-CB9H8]- regioselectively from [1,2-Me2-1,2-closo-C2B 10H10]. First, the o-carborane derivative is reduced to [7-Me-μ-(9,10-HMeC)-7-nido-CB10H11]-, and then a carbon-atom extrusion followed by selective deboronation takes place.
Reduction of hydroxy-functionalised carbaboranyl carboxylic acids and ketones by organolithium reagents
Neumann,Hiller,Sárosi,L?nnecke,Hey-Hawkins
, p. 6638 - 6644 (2015)
While the reaction of carbaboranyl carboxylic acids and ketones with organolithium reagents generally leads to cleavage of the exo-polyhedral C-C bond, introduction of a hydroxyl group at the second carbon atom of the cluster enables the reduction of the carbonyl compounds to tertiary alcohols. The proposed mechanism involving the formation of dimeric contact ion pairs was supported by X-ray crystallography and theoretical calculations. This journal is
A new series of organoboranes. I. Carboranes from the reaction of decaborane with acetylenic compounds
Heying,Ager Jr.,Clark,Mangold,Goldstein,Hillman,Polak,Szymanski
, p. 1089 - 1092 (1963)
Decaborane and certain of its derivatives reacted with acetylenic compounds in the presence of Lewis bases to produce members of a new class of organoboranes. The parent compound 1,2-dicarbaclovododecaborane(12) has the formula B10C2H12 and various C and B substituted derivatives are reported. Unlike other higher boranes, this nucleus is quite impervious to attack by compounds containing active hydrogen and it does not attack reducible groups such as carbonyl or nitrite.
The BI activation in o-carborane clusters: their fate towards BH. Easy synthesis of [7,10-C2B10H13]-
Vi?as, Clara,Barberà, Gemma,Teixidor, Francesc
, p. 16 - 19 (2002)
The reaction of 3-I-o-carborane with Cu, Cu/PPh3, [Ni(PPh3)3], or [Pd(PPh3)4] has been studied to find the suitability of B-iodine substituted carboranes as sources of new boron-derivatives. In all these reactions a hydrodehalogenation reaction to yield o-carborane has been produced, indicating that BI activation takes place. It may be considered that BI adds oxidatively to M, but alternative explanations can be given. Reaction of 3-I-o-carborane with Na/naphthalene also produced o-carborane showing that albeit an oxidative addition is impossible for sodium the same hydrodehalogenation had taken place. The same result was also formed with Mg. Addition of 1,2-dibromoethane to the Mg/o-carborane reaction yielded [7,10-C2B10H13]-. Then, the sequence 3-I-o-carborane→o-carborane→[7,10-C2B10H13]- can be generated with only reducing agents. The synthetic procedure for [7,10-C2B10H13]- is very simple and produces a 97% yield of [NMe4][7,10-C2B10H13]. Basically, 1,2-C2B10H12 and Mg in excess are refluxed in THF in the presence of I2 and 1,2-dibromoethane.
Preparation and Properties of Inclusion Complexes of 1,2-Dicarbadodecaborane(12) with Cyclodextrins
Harada, Akira,Takahashi, Shigetoshi
, p. 1352 - 1353 (1988)
One-to-one inclusion complexes were obtained in a crystalline state in high yields by treatment of β- and γ-cyclodextrin with 1,2-dicarbadodecaborane(12) (o-carborane), whereas α-cyclodextrin formed a 2:1 (cyclodextrin: guest) complex on sonication, and a 1:1 complex on crystallization from water-propan-2-ol.
