A 18 Acidic hydrolysis of N-acyl-1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes [Electronic resource] / G. L. Levit, A. M. Demin, M. I. Kodess, M. A. Ezhikova, L. Sh. Sadretdinova, V. A. Ol'shevskaya, V. N. Kalinin, V. P. Krasnov, V. N. Charushin // Journal of Organometallic Chemistry. - 2005. - Vol. 690, № 11. - P2783-2786 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Acidic hydrolysis of N-acyl 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes has been studied. It has been shown that acidic hydrolysis of diastereomeric amides of 1-methyl-3-amino-1,2-dicarba-closo-dodecaborane results in the partial racemization of the target 3-amino-1-methylcarborane. Under the similar conditions, the hydrolysis of N-acyl-3-amino-1-phenyl-1,2-dicarba-closo-dodecaboranes resulted in amide bond cleavage accompanied by simultaneous deboronation with the removal of boron atom at position 6 of carborane cage and formation of 7,8-dicarba-nido-undecaborane derivative according to 11B and 1H NMR spectroscopy. \\\\Expert2\\nbo\\Journal of Organometallic Chemistry\\2005, v. 690, p.2783.pdf |
C 21 Carborane-Functionalized Polyaza Aromatic Ligands: Synthesis, Crystal Structure, and a Copper(II) Complex [Text] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, I. V. Glukhov, M. Yu. Antipin, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko // Organometallics. - 2006. - Vol. 25, № 12. - P2972-2977 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A consecutive aromatic nucleophilic substitutions of hydrogen in 1,2,4-triazine 4-oxides and an aza Diels?Alder reaction is a versatile route to carborane-functionalized bi- and terpyridines and their 1,2,4-triazine analogues. The heterocycles facilitate deboronation of the substituted carboranes, and the carborane moiety has a significant influence on the coordination properties of the ligands as well |
L 81 Lithiacarboranes and 1,2,4-triazine 4-oxides: SNH reactions and ring transformations [Electronic resource] / O. N. Chupakhin, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, I. A. Glukhov, Z. A. Starikova, V. A. Ol'shevskaya, V. N. Kalinin, M. Yu. Antipin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1223-1231. - Библиогр. : с. 1231 (14 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 1-lithia-1,2- or 1,7-dicarba-closo-dodecaborane with 1,2,4-triazine 4-oxides can follow two competitive pathways: deoxygenative nucleophilic substitution of hydrogen to form 1-(1,2,4-triazin-5-yl)-1,2- or 1,7-dicarba-closo-dodecaboranes and the transformation of the 1,2,4-triazine ring into the triazoline ring giving rise to 1-(2-acetyl-1-aroyl-3-aryl-1,2,4-triazolin-5-yl)-1,2-dicarba-closo-dodecaboranes. Introduction of the electron-withdrawing triazine ring into the carborane cage substantially facilitates deboronation to give 1-(1,2,4-triazin-5-yl)-1,2-1,7-dicarba-nido-undecaboranes. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1223-1231.pdf |
S 98 Synthesis of a novel planar-chiral nido-carborane amino acid / A. A. Telegina, D. A. Gruzdev, G. L. Levit, V. P. Krasnov // Russian chemical bulletin. - 2021. - Vol. 70, № 3. - P539-544 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBORANE -- PLANAR CHIRALITY -- AMINO ACID -- DEBORONATION Аннотация: The deboronation of enantiomers of planar-chiral benzyl (3-formamido-1,2-dicarba-closo-dodecaboran-1-yl)acetate gave the individual (RP)- and (SP)-enantiomers (ee > 98%) of a new amino acid containing a nido-carborane fragment, (3-ammonio-7,8-dicarba-nido-undecaboran-7-yl)acetic acid. Chiral HPLC methods for the analysis of enantiomeric purity of this compound was developed. |
N-aminoacyl-3-amino-nido-carboranes as a group of boron-containing derivatives of natural amino acids / D. A. Gruzdev, A. A. Telegina, G. L. Levit, V. P. Krasnov // Journal of Organic Chemistry. - 2022. - Vol. 87, № 8. - P5437-5441 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new group of nido-carboranyl derivatives of natural (S)-amino acids containing from 9 to 18 boron atoms was obtained in good yields as a result of acylation of 3-amino-1,2-dicarba-closo-dodecaborane followed by deboronation. The proposed approach is convenient and based on the use of readily available reagents and is suitable for the synthesis of enantiopure nido-carboranyl derivatives of amino acids with various side chains, including water-soluble boron-containing amino acids (17 examples). |