Synthesis of monosubstituted functional derivatives of carboranes from 1-mercapto-ortho-carborane: 1-HOOC(CH2)nS-1,2-C2B10H11and [7-HOOC(CH2)nS-7,8-C2B9H11]−(n = 1–4)
- 23 December 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Dalton Transactions
- Vol. 39 (7), 1817-1822
- https://doi.org/10.1039/b916022a
Abstract
A general approach to synthesis of monosubstituted functional derivatives of 1,2-dicarba-closo-dodecaborane (ortho-carborane) is proposed. Reactions of the triethylammonium salt of 1-mercapto-ortho-carborane (Et3NH)[1-S-1,2-C2B10H11] with ethyl ω-bromoalkyl carboxylates and ω-bromoalkylnitriles in ethanol result in the corresponding carboranyl esters and nitriles that in turn can be converted to carborane-based carboxylic acids 1-HOOC(CH2)nS-closo-1,2-C2B10H11 (n = 1–4). Mild deboronation of the closo-carborane cage with CsF in ethanol gives caesium salts of the corresponding nido-carboranes Cs[7-HOOC(CH2)nS-nido-7,8-C2B9H11]. This approach is suitable for synthesis of compounds to be used in boron neutron capture therapy and radionuclide diagnostics of cancer.Keywords
This publication has 57 references indexed in Scilit:
- Permeability of the Blood-Brain Barrier to a RhenacarboraneThe Journal of pharmacology and experimental therapeutics, 2009
- Carborane-carbohydrate derivatives — Versatile platforms for developing targeted radiopharmaceuticalsCanadian Journal of Chemistry, 2008
- A Novel Dinuclear Ruthenium(I)/Ruthenium(III) Half-Sandwich Complex Containing Two Chelating 1,2-Dicarba-closo-dodecaborane-1,2-dithiolate Ligands and Its Reactivity with AlkynesOrganometallics, 2007
- Synthesis of Functional Derivatives of 7,8-Dicarba-nido-undecaborate Anion by Ring-Opening of Its Cyclic Oxonium DerivativesCollection of Czechoslovak Chemical Communications, 2007
- Probing the Electronic Structure of Platinum(II) Chromophores: Crystal Structures, NMR Structures, and Photophysical Properties of Six New Bis- and Di- Phenolate/Thiolate Pt(II)Diimine ChromophoresInorganic Chemistry, 2006
- Synthesis, reactivity and structural studies of carboranyl thioethers and disulfidesDalton Transactions, 2005
- Chameleonic Capacity of [3,3‘-Co(1,2-C2B9H11)2]-in Coordination. Generation of the Highly Uncommon S(thioether)−Na BondOrganometallics, 2003
- Chemistry of closo-Dodecaborate Anion [B12H12]2-: A ReviewCollection of Czechoslovak Chemical Communications, 2002
- Facile and Mild Deboronation ofo-Carboranes Using Cesium FluorideInorganic Chemistry, 2001
- A Route to exo-Heterodisubstituted and Monosubstituted o-Carborane DerivativesInorganic Chemistry, 1997