Abstract
A determination of enantiomeric purity of 1-substituted (Me, Ph, and Pri) 3-amino-1,2dicarba-closo-dodecaboranes by HPLC on chiral Chiralcel OD-H and Chiralpac AD stationary phases involving preliminary phthaloylation of 3-aminocarboranes has been suggested as a general method.
Similar content being viewed by others
References
V. I. Bregadze, Chem. Rev., 1992, 92, 209.
I. B. Sivaev, V. I. Bregadze, Ros. Khim. Zh., 2004, 48, 109 [Mendeleev Chem. J., 2004, 48 (Engl. Transl.)].
M. F. Hawthorne, Angew. Chem., Int. Ed. Engl., 1993, 32, 950.
A. H. Soloway, W. Tjarks, B. A. Barnum, F.-G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson, Chem. Rev., 1998, 98, 1515.
J. F. Valliant, K. J. Guenther, A. S. King, P. Morel, P. Schaffer, O. O. Sogbein, K. A. Stephenson, Coord. Chem. Rev., 2002, 232, 173.
B. Grüner, Z. Plzák, J. Chromatogr. A, 1997, 789, 497.
J. H. Kindsvater, P. H. Weiner, T. J. Klingen, Anal. Chem., 1974, 46, 982.
W. J. Evance, M. F. Hawthorne, J. Chromatogr. A, 1974, 88, 187.
J. Čoupek, S. Pokorny, V. Gregor, V. V. Jehlička, J. Chromatogr. A, 1974, 88, 323.
J. Plešek, B. Grüner, P. Maloň, J. Chromatogr. A, 1992, 626, 197.
J. Plešek, B. Grüner, P. Maloň, Collect. Czech. Chem. Commun., 1993, 58, 1087.
J. Plešek, B. Grüner, T. Vaněk, H. Votavová, J. Chromatogr. A, 1993, 633, 73.
J. Plešek, B. Grüner, J. Fusek, H. Votavová, Collect. Czech. Chem. Commun., 1993, 58, 2936.
J. Plešek, B. Grüner, S. Heřmánek, J. Fusek, H. Votavová, Collect. Czech. Chem. Commun., 1994, 59, 374.
B. Grüner, J. Holub, J. Plešek, T. Vaněk, H. Votavová, J. Chromatogr. A, 1998, 793, 249.
M. M. Il’in, T. V. Zinevich, I. V. Pisareva, I. T. Chizhevskii, V. A. Davankov, Izv. Akad. Nauk, Ser. Khim., 2000, 759 [Russ. Chem. Bull., Int. Ed., 2000, 49, 759].
E. Yashima, J. Chromatogr. A, 2001, 906, 105.
V. P. Krasnov, G. L. Levit, V. N. Charushin, A. N. Grishakov, M. I. Kodess, V. N. Kalinin, V. A. Ol’shevskaya, O. N. Chupakhin, Tetrahedron: Asymmetry, 2002, 13, 1833.
G. L. Levit, V. P. Krasnov, A. M. Demin, M. I. Kodess, L. Sh. Sadretdinova, T. V. Matveeva, V. A. Ol’shevskaya, V. N. Kalinin, O. N. Chupakhin, V. N. Charushin, Mendeleev Commun., 2004, 14, 293.
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, J. Organomet. Chem., 2005, 690, 2783.
H. Spahn, D. D. Krauß, E. Mutschler Pharm. Res., 1988, 5, 107.
H. Spahn, Arch. Pharm. (Weinheim Ger.), 1988, 321, 847.
N. Büyüktimkin, A. Buschauer, J. Chromatogr. A, 1988, 450, 281.
E. Martin, K. Quinke, H. Spahn, E. Mutschler, Chirality, 1989, 1, 223.
H. Spahn, W. Henke, P. Langguth, J. Schloos, E. Mutschler, Arch. Pharm. (Weinheim Ger.), 1990, 323, 465.
K. Haaf, C. Rüchardt, Chem. Ber., 1990, 123, 635.
A. Solis, H. Luna, H. I. Perez, N. Manjarrez, R. Sanchez, A. Gutierrez, Tetrahedron Lett., 1998, 39, 8759.
K. P. Cole, R. P. Hsung, Tetrahedron Lett., 2002, 43, 8791.
K. Błažewska, T. Gajda, Tetrahedron: Asymmetry, 2002, 13, 671.
V. P. Krasnov, G. L. Levit, I. M. Bukrina, A. M. Demin, O. N. Chupakhin, J. U. Yoo, Tetrahedron: Asymmetry, 2002, 13, 1911.
L. I. Zakharkin, V. A. Ol’shevskaya, D. D. Sulaimankulova, V. A. Antonovich, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1151 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 1026 (Engl. Transl.)].
J. C. Sheehan, D. W. Chapman, R. W. Roth, J. Am. Chem. Soc., 1952, 74, 3822.
G. M. Sheldrick, SADABS, V2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS Inc., Madison, WI 1998.
G. M. Sheldrick, SHELXTL, V5.10, Bruker AXS Inc., Madison, WI, 1998.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2484–2488, December, 2008.
Rights and permissions
About this article
Cite this article
Krasnov, V.P., Demin, A.M., Levit, G.L. et al. Determination of enantiomeric purity of 1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes by HPLC on chiral stationary phases. Russ Chem Bull 57, 2535–2539 (2008). https://doi.org/10.1007/s11172-008-0364-5
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-008-0364-5