Zwitterionic Phosphoranides as Intermediates in the Reaction of Phosphorus Tribromide with N,N-Dimethyl-N′-arylformamidines
Anatoliy P. Marchenko
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorGeorgyi N. Koidan
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorAnastasia N. Hurieva
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorAlexander B. Rozhenko
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorCorresponding Author
Aleksandr N. Kostyuk
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Correspondence to: Aleksandr N. Kostyuk; e-mail: [email protected].Search for more papers by this authorAnatoliy P. Marchenko
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorGeorgyi N. Koidan
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorAnastasia N. Hurieva
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorAlexander B. Rozhenko
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Search for more papers by this authorCorresponding Author
Aleksandr N. Kostyuk
Institute of Organic Chemistry, Kyiv, 02094 Ukraine
Correspondence to: Aleksandr N. Kostyuk; e-mail: [email protected].Search for more papers by this authorABSTRACT
Cyclic zwitterionic phosphoranides 2a,b were found to be intermediate products in the reaction of N,N-dimethyl-N′-(aryl)formamidines with PBr3. The structure of phosphoranide 2a was determined by means of the X-ray and quantum chemistry investigations. Mechanism of its formation was proposed based on Density functional theory (DFT) calculations. Reactions of 2 with amines and selenium yielded either C-phosphorylated formamidines or benzazaphospholes. The first example of intramolecular heterocyclization of a pentavalent phosphorus derivative 15b into 3Н-1,3-benzazaphosphole has been demonstrated.
Supporting Information
Disclaimer: Supplementary materials have been peer-reviewed but not copyedited.
| Filename | Description |
|---|---|
| hc21283-sup-0001-SuppMat.zip409.5 KB | Table S1. Crystal data and structure refinement for 2a, 12b and 14b. Table S2. Calculated bond lengths (Å) and bond angles (degrees) for 2a,c. Table S3. Calculated total energies (E), ZPE correction to total energy values (ZPE), ZPE corrected total energies (E+ZPE) and the lowest vibration frequencies (ν) for 2a,c. |
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REFERENCES
- 1Sheldrick, W. S.; Schmidpeter, A.; Zwaschka, F.; Dillon, K. B.; Platt, A. W. G.; Waddington, T. C. J Chem Soc, Dalton Trans 1981, 413.
- 2Christe, K. O.; Dixon, D. A.; Mercier, H. P. A.; Sanders, J. C. P.; Schrobilgen, G. J.; Wilson, W. W. J Am Chem Soc 1994, 116, 2850–2858.
- 3Shyshkov, O. A. Ph.D. Thesis; University of Bremen, 2006; 177 p.
- 4Karsch, H. H.; Witt, E.; Hahn, F. E. Angew Chem, Int Ed 1996, 35, 2242–2244.
- 5Schwedtmann, K.; Holthausen, M. H.; Feldmann, K.-O.; Weigand, J. J. Angew Chem, Int Ed 2013, 52, 14204–14208.
- 6Wang, Y.; Xie, Y.; Abraham, M. Y.; Gilliard, R. J.; Wei, P.; Schaefer, H. F.; Schleyer, P.v.R.; Robinson, G. H. Organometallics 2010, 29, 4778–4780.
- 7Dillon, K. B.; Platt, A. W. G.; Schmidpeter, A.; Zwaschka, F.; Sheldrick, W. S. Z Anorg Allg Chem 1982, 488, 7–26.
- 8Müller, G.; Matheus, H.-J.; Winkler, M. Z Naturforsch 2001, 56b, 1155–1162.
- 9Müller, G.; Brand, J.; Jetter, S. E. Z Naturforsch 2001, 56b, 1163–1171.
- 10Surgenor, B. A.; Bühl, M.; Slawin, A. M. Z.; Woollins, J. D.; Kilian, P. Angew Chem, Int Ed 2012, 51, 10150–10153.
- 11Kilian, P.; Knight, F. R.; Woollins, J. D. Chemistry 2011, 17, 2302–2328.
- 12Wawrzyniak, P.; Fuller, A. L.; Slawin, A. M. Z.; Kilian, P. Inorg Chem 2009, 48, 2500–2506.
- 13Carré, F. H.; Chuit, C.; Corriu, R. J. P.; Douglas, W. E.; Guy, D. M. H.; Reyé, C. Eur J Inorg Chem 2000, 2000, 647–653.
10.1002/(SICI)1099-0682(200004)2000:4<647::AID-EJIC647>3.0.CO;2-N Google Scholar
- 14Chuit, C.; Reyé, C. Eur J Inorg Chem 1998, 1998, 1847–1857.
10.1002/(SICI)1099-0682(199812)1998:12<1847::AID-EJIC1847>3.0.CO;2-K Google Scholar
- 15Dillon, K. B. Chem Rev 1994, 94, 1441–1456.
- 16Ellis, B. D.; Macdonald, C. L. B. Coord Chem Rev 2007, 251, 936–973.
- 17Tolmachev, A. A.; Merkulov, A. S.; Oshovskii, G. V. Chem Heterocycl Compd 1997, 33, 877–878.
- 18(a) Marchenko, A.; Koidan, H.; Hurieva, A.; Merkulov, A.; Pinchuk, A.; Yurchenko, A.; Rozhenko, A. B.; Jones, P. G.; Thönnessen, H.; Kostyuk, A. Tetrahedron 2011, 67, 7748–7758 (b) Marchenko, A.; Koidan, H.; Hurieva, A.; Merkulov, A.; Pinchuk, A.; Yurchenko, A.; Kostyuk, A. Tetrahedron 2010, 66, 3668–3677.
- 19Kuchitsu, K.; Shibata, T.; Yokozeki, A.; Matsumura, C. Inorg Chem 1971, 10, 2584–2587.
- 20Tao, J.; Perdew, J.; Staroverov, V.; Scuseria, G. Phys Rev Lett 2003, 91, 146401.
- 21Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P. J Chem Phys 2003, 119, 12129.
- 22Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. Chem Phys Lett 1998, 294, 143–152.
- 23Mayer, I. Int J Quantum Chem 1984, 26, 151–154.
- 24Marchenko, A.; Koidan, G.; Hurieva, A.; Savateev, A.; Rozhenko, A. B.; Sotiropoulos, J.-M.; Shishkina, S. V.; Shishkin, O. V.; Kostyuk, A. Eur J Inorg Chem 2014, 2014, 1192–1203.
- 25Marchenko, A.; Koidan, G.; Hurieva, A.; Kurpiieva, O.; Vlasenko, Y.; Rozhenko, A. B.; Kostyuk, A. Eur J Inorg Chem 2014, 2014, 3259–3270.
- 26Neese, F. Wiley Interdiscip Rev Comput Mol Sci 2012, 2, 73–78.
- 27Schäfer, A.; Huber, C.; Ahlrichs, R. J Chem Phys 1994, 100, 5829–5835.
- 28Neese, F.; Wennmohs, F.; Hansen, A.; Becker, U. Chem Phys 2009, 356, 98–109.
- 29Izsák, R.; Neese, F. J Chem Phys 2011, 135, 144105.
- 30Jmol: an open-source Java viewer for chemical structures in 3D. Available at http://www.jmol.org/.
