title: Synthesis of monosubstituted functional derivatives of carboranes from 1-mercapto-ortho-carborane: 1-HOOC(CH(2))(n)S-1,2-C(2)B(10)H(11) and [7-HOOC(CH(2))(n)S-7,8-C(2)B(9)H(11)](-) (n = 1-4).
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 (Et(3)NH)[1-S-1,2-C(2)B(10)H(11)] with ethyl omega-bromoalkyl carboxylates and omega-bromoalkylnitriles in ethanol result in the corresponding carboranyl esters and nitriles that in turn can be converted to carborane-based carboxylic acids 1-HOOC(CH(2))(n)S-closo-1,2-C(2)B(10)H(11) (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(CH(2))(n)S-nido-7,8-C(2)B(9)H(11)]. This approach is suitable for synthesis of compounds to be used in boron neutron capture therapy and radionuclide diagnostics of cancer.
authors.affiliation: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991, Moscow, Russia.
authors.forename: Marina Yu
authors.initials: MY
authors.lastname: Stogniy
authors.forename: Igor B
authors.initials: IB
authors.lastname: Sivaev
authors.forename: Pavel V
authors.initials: PV
authors.lastname: Petrovskii
authors.forename: Vladimir I
authors.initials: VI
authors.lastname: Bregadze
mesh_terms: D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001880:Boranes; D013438:Sulfhydryl Compounds