New phosphorus-containing quinone derivatives
Patrick Müller
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorYana Bykov
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorOlaf Walter
European Commission Joint Research Centre, Institute for Transuranium Elements, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorCorresponding Author
Manfred Döring
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, GermanySearch for more papers by this authorPatrick Müller
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorYana Bykov
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorOlaf Walter
European Commission Joint Research Centre, Institute for Transuranium Elements, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorCorresponding Author
Manfred Döring
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, GermanySearch for more papers by this authorAbstract
A variety of new aromatic diols substituted with two (similar and different) phosphorus groups were synthesized via the Michael-type addition of a PH bond containing reagents to p-benzoquinone, reoxidation and the subsequent addition of a second phosphorus unit. In all studied cases, 2,3-substituted products were obtained exclusively. The resulting hydroquinone derivatives were further investigated regarding rearrangements under basic conditions. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:383–394, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21028
REFERENCES
- 1 Pudovik, A. N.; Konovalova, I. V. Synthesis 1979, 81–96.
- 2 Tanaka, M. J. Top Curr Chem 2004, 232, 25–54.
- 3 Alonso, F.; Beletskaya, I. P.; Yus, M. Chem Rev 2004, 104, 3079–3159.
- 4 Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur J Org Chem 2006, 29–49.
- 5
Enders, D.;
Tedeschi, L.;
Bats, J. W.
Angew Chem, Int Ed
2000, 39, 4605–4607.
10.1002/1521-3773(20001215)39:24<4605::AID-ANIE4605>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 6 Stockland, R. A.; Taylor, R. I.; Thompson, L. E.; Patel, P. B. Org Lett 2005, 7, 851–853.
- 7 Keglevich, G.; Sipos, M.; Takács, D.; Greiner, I. Heteroatom Chem 2007, 18, 226–229.
- 8 Keglevich, G.; Sipos, M.; Takács, D.; Ludányi, K. Heteroatom Chem 2008, 19, 288–292.
- 9 Bálint, E.; Takács, J.; Drahos, L.; Keglevich, G. Heteroatom Chem 2012, doi: 10.1002/hc.21007.
- 10 Keglevich, G.; Sipos, M.; Imre, T.; Ludányi, K.; Szieberth, D.; Toke, L. Tetrahedron Lett 2002, 43, 8515–8518.
- 11 Keglevich, G.; Sipos, M.; Szieberth, D.; Nyulászi, L.; Imre, T.; Ludányi, K.; Toke, L. Tetrahedron 2004, 60, 6619–6627.
- 12
Kutyrev, A. A.;
Moskva, V. V.
Russ Chem Rev
1987, 56(11), 1028–1044.
10.1070/RC1987v056n11ABEH003320 Google Scholar
- 13 Kutyrev, A. A. Russ J Gen Chem 1996, 66(3), 474–490.
- 14 Kutyrev, A. A. Tetrahedron 1991, 47(38), 8043–8065.
- 15 Rakotomalala, M.; Wagner, S.; Döring, M. Materials 2010, 3, 4300–4327.
- 16 Wang, C. S.; Lin, C. H.; Chen, C. Y. J Polym Sci, Part A: Polym Chem 1998, 36, 3051–3061.
- 17 Wang, C. H.; Lin, C. S. Polymer 1999, 40, 747–757.
- 18 Xia, X.-N.; Lu, Y.-B.; Zhou, X.; Xiong, Y.-Q.; Zhang, X.-H.; Xu, W.-J. J Appl Polym Sci 2006, 102, 3842–3847.
- 19 Spontón, M.; Ronda, J. C.; Galià, M.; Cádiz, V. J Polym Sci, Part A: Polym Chem 2007, 45, 2142–2151.
- 20 Worku, A.; Bharadwaj, A.; Thibault, R.; Wilson, M.; Potts, D. WO Patent 2010025165, 2010.
- 21 Brehme, S.; Schartel, B.; Goebbels, J.; Fischer, O.; Pospiech, D.; Bykov, Y.; Döring, M. Polym Deg Stab 2011, 96, 875–884.
- 22 Fischer, O.; Pospiech, D.; Korwitz, A.; Sahre, K.; Häußler, L.; Friedel, P.; Fischer, D.; Harnisch, C.; Bykov, Y.; Döring, M. Polym Deg Stab 2011, 96(12), 2198–2208.
- 23 Pudovik, A. N.; Romanov, G. V.; Pozhidev, V. M. Russ Chem Bull 1978, 27(7), 1450–1452.
- 24 Trutneva, E. K.; Levin, Ya. A. Russ Chem Bull 1983, 32(7), 1532–1533.
- 25 Nifanùev, E. E.; Kukhareva, T. S.; Davydochkina, O. V. Zh Obsch Khim 1992, 62, 222–223.
- 26 Dhawan, B.; Redmore, D. J Org Chem 1984, 49, 4018–4021.
- 27 Griffin, C. E.; Davison, R. B.; Gordon, M. Tetrahedron 1966, 22, 561–566.
- 28 Saito, T. U.S. Patent 3702878, 1972.
- 29 Schartel, B.; Balabanovich, A. I.; Braun, U.; Knoll, U.; Artner, J.; Ciesielski, M.; Döring, M.; Perez, R.; Sandler, J. K. W.; Altstädt, V.; Hoffmann, T.; Pospiech, D. J Appl Polym Sci 2007, 104(4), 2260–2269.
- 30 Perret, B.; Schartel, B.; Stöß, K.; Ciesielski, M.; Diederichs, J.; Döring, M.; Krämer, J.; Altstädt, V. Macromol Mater Eng 2011, 296(1), 14–30.
- 31 Perret, B.; Schartel, B.; Stöß, K.; Ciesielski, M.; Diederichs, J.; Döring, M.; Krämer, J.; Altstädt, V. Eur Polym J 2011, 47(5), 1081–1089.
- 32 Ueda, A.; Matsumoto, T.; Imamura, T.; Tsujimoto, K. Japan Patent 63185992, 1988.
- 33 Bharucha, K. R. J Chem Soc 1956, 2446–2447.
- 34 Su, W.-C.; Sheng, C.-S. U.S. Patent 2005101793A1, 2005.
- 35 Howell, B. A.; Carter, K. E. Polym Prepr 2010, 51(1), 755–756.
- 36 Ostwald, A. A. Can J Chem 1959, 45, 1498–1506.
- 37 SADABS, Siemens, 1997.
- 38 SHELX-97, G. Sheldrick, University of Göttingen, Germany, 1997. Available at http://shelx.uni-ac.gwdg.de/SHELX (accessed on September 21 2011).
- 39 Xpma, Zsolnai, L.; Huttner, G. University of Heidelberg, Germany, 1997. Available at http://www.aci.uni-heidelberg.de/aci_sub (accessed on September 21, 2011).
- 40 Mercury 2.4, Cambridge Crystallographic Data Centre, UK, 2010.