Preparation and properties of 1-hydroxycarboranes

Zakharkin, L. I.; Zhigareva, G. G.

doi:10.1007/bf00861488

Cited by 11 publications

(33 citation statements)

References 3 publications

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“…38 The strong electron withdrawing effect of the 1 o car boranyl group is responsible for high acidity of C car boxy , C hydroxy , and C mercaptocarboranes. [39][40][41] The high acidity of 1 hydroxy o carborane was con firmed 42 by measurements of pK a during titration of a 50% ethanolic solution of this compound with aqueous NaOH.…”

Section: Methodsmentioning

confidence: 99%

Some aspects of the chemical behavior of icosahedral carboranes

Калинин

Ol’shevskaya

2008

Russ Chem Bull

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Important features of the chemical behavior of icosahedral carboranes are considered. The ways of introducing functional groups at the carbon and boron atoms of carboranes by conventional methods of organic chemistry and methods applicable only to carboranes are discussed. The latter methods include transformations of dicarbadodecaborate (14) dianions. Examples of the enantiomer ic resolution of optically active carboranes, whose chirality is associated with the molecular asym metry, are given. The diversity of chemical transformations of carboranes is exemplified by in tramolecular nucleophilic rearrangements, cross coupling reactions, and the formation of chelate metallacycles.

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Section: Methodsmentioning

confidence: 99%

Some aspects of the chemical behavior of icosahedral carboranes

Калинин

Ol’shevskaya

2008

Russ Chem Bull

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“…Direct C-oxygenation has been accomplished by reacting carboranyllithium with oxygen 114 or peroxides 115 among which trimethylsilyl peroxide was found to work best, giving yields of the C-hydroxy-para-carborane up to 30% (refs 88,116 ). An even more efficient method for introduction of the hydroxy group through the oxidation of the corresponding C-boronic acid was reported recently (Scheme 6) 88 .…”

Section: Carbon Substitutionmentioning

confidence: 99%

“…The O-anions derived from highly acidic carboranyl OH groups 115,116 are rather poor nucleophiles and they react well with strong alkylation reagents such as diazomethane 115 , dimethylsulfate ([1-(OH) 2 -CB 11 H 11 ]) (ref. 67 ), and allyl iodide 116 .…”

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confidence: 99%

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Four Decades of Organic Chemistry of closo-Boranes: A Synthetic Toolbox for Constructing Liquid Crystal Materials. A Review

Kaszyński

1999

Collect. Czech. Chem. Commun.

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Introduction and transformations of organic functional groups to ten- and twelve-vertex closo-boranes and heteroboranes is reviewed in the context of preparation of liquid crystalline compounds. The review, containing 198 references, is designed as a synthetic manual for materials chemists and focuses on methods for engineering molecules with elongated shapes and variable dipole moments. Several underdeveloped aspects of closo-borane chemistry are identified.

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“…[1][2][3][4][5][6] Since the discovery of their catalytic activity, 7 they have been widely applied as the catalyst precursors in numerous organic processes. [8][9][10][11][12] The fi rst 12-vertex 3,1,2-[(PPh 3 ) 2 OsHXC 2 B 9 H 11 ] (X = Cl and H) and 3,1,2-[(PPh 3 ) 2 OsH 2 -1,2-Me 2 C 2 B 9 H 9 ] closohydridoosmacarboranes were synthesized via the reaction of (PPh 3 ) 3 OsCl 2 (1) with K + salts of [nido-7,8-R 2 -7,8-C 2 B 9 H 10 ]nido-anions (R = H and Me) in ethanol upon refl ux. 13 The reaction of complex 1 with [7-R-nido-7,9-C 2 B 9 H 11 ]anions (R = H and Ph) in benzene at room temperature proceeds with the formation of 16-electron [exo-nido-10,11-{(Ph 3 P) 2 OsHCl}-10,11-(μ-H) 2 -7-R-7,9-C 2 B 9 H 8 ] chlorohydride osmacarboranes (R = H and Ph) of the exo-nido-structure and small amounts of chargecompensated [7-R-nido-7,9-C 2 B 9 H 10 PPh 3 ] nido-carboranes.…”

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confidence: 99%