Investigation of N- and C-Phosphanylation of [1,2,4]Triazolo[4,3-a]pyridines
Anatoliy P. Marchenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorHeorgiy N. Koidan
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorAndrey A. Kirilchuk
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorAlexander B. Rozhenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Fakultät für Chemie der Universität Bielefeld, 33615 Bielefeld, Germany
Search for more papers by this authorAleksandr A. Yurchenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorCorresponding Author
Aleksandr N. Kostyuk
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Correspondence to: Alexandr N. Kostyuk; e-mail: [email protected].Search for more papers by this authorAnatoliy P. Marchenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorHeorgiy N. Koidan
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorAndrey A. Kirilchuk
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorAlexander B. Rozhenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Fakultät für Chemie der Universität Bielefeld, 33615 Bielefeld, Germany
Search for more papers by this authorAleksandr A. Yurchenko
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Search for more papers by this authorCorresponding Author
Aleksandr N. Kostyuk
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kyiv-94, 02094 Ukraine
Correspondence to: Alexandr N. Kostyuk; e-mail: [email protected].Search for more papers by this authorABSTRACT
Synthesis and deprotonation of N-phosphanylated[1,2,4]triazolo[4,3-a]pyridinium triflates were investigated. Phosphanylation by t-Bu2PCl proceeds at N1 of starting triazolo-pyridines. According to density functional theory calculations, deprotonation of the formed salt gives abnormal carbenes, which decompose by opening of the triazole cycle. Treatment by chlorodiphenylphosphane leads to an equilibrium mixture of N1- and N2-phosphanylated salts, which under addition of base yields normal carbene that rapidly rearranges to form C-phosphanylated product. Mechanisms of the reactions are discussed.
Supporting Information
Disclaimer: Supplementary materials have been peer-reviewed but not copyedited.
| Filename | Description |
|---|---|
| hc21258-sup-0001-SuppMat.doc5.8 MB | Table S1. Calculated (RI-BP86/TZVP) total energy values (E, a.u.), zero-point energy correction (ZPE, a.u.) and thermal correction to Gibbs free energy (TCGFE, a.u.) magnitudes, corrected total energy values (E+ZPE and E+ TCGFE) and the lowest vibration frequencies (ν, cm-1) of compounds 1-17. Figure S1. Structure of transition state 8a-TS from calculations data. |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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