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2-DIETHYLAMINOVINYL DERIVATIVES OF HALOGENATED 1,4-QUINONES: SYNTHETIC AND STRUCTURAL ASPECTS

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Abstract

Diethylaminovinyl derivatives of halogenated 1,4-quinones (enaminoquinones) are produced by the interaction of halogenated 1,4-quinones with N,N-diethyl-N-vinylamine obtained in situ from Et2NH and MeCHO. Molecular and crystal structures of enaminoquinones halogenated in the quinone fragment are determined. It is shown that in the solid phase, atoms of the entire push-pull system of enaminoquinones lie practically in one plane.

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REFERENCES

  1. H. S. Nalwa. Adv. Mater., 1993, 5, 341–358.

  2. J. L. Brédas, C. Adant, P. Tackx, and A. Persoons. Chem. Rev., 1994, 94, 243–278.

  3. S. D. Bella, I. L. Fragalá, M. A. Ratner, and T. J. Marks. J. Am. Chem. Soc., 1993, 115, 682–686.

  4. R. Pilot and R. Bozio. Phys. Chem. Chem. Phys., 2011, 13, 230–239.

  5. B. I. Kidyarov, V. V. Atuchin, and N. V. Pervukhina. J. Struct. Chem., 2010, 51(6), 1119–1125.

  6. R. M. Metzger and C. A. Panetta. New J. Chem., 1991, 15, 209–221.

  7. A. Aviram. Molecular Electronic Science and Technology. Engineering Foundation: New York, 1989.

  8. S .R. Marder and J. W. Perry. Adv. Mater., 1993, 5, 804–815.

  9. J. A. Cowan, J. K. M. Sanders, G. S. Beddard, and R. J. Harrison. J. Chem. Soc., Chem. Commun., 1987, 55–58.

  10. D. Gust and T. A. Moore. Science, 1989, 244, 35–41.

  11. H. Tamiaki and K. Maruyama. J. Chem. Soc. Perkin Trans1, 1992, 2431–2435.

  12. B. Illescas, N. Martín, J. L. Segura, and C. Seoane. J. Org. Chem., 1995, 60, 5643–5650.

  13. E. P. Fokin and E. P. Prudchenko. Zh. Org. Khim., 1970, 6, 91–93.

  14. E. P. Fokin and E. P. Prudchenko. Zh. Org. Khim., 1970, 6, 1251–1255.

  15. D. Buckley, S. Dunstan, and H. B. Henbest. J. Chem. Soc., 1957, 4880–4891.

  16. L. I. Goryunov, N. M. Troshkova, G. A. Nevinskii, and V. D. Shteingarts. Russ. J. Org. Chem., 2009, 45, 835–841.

  17. M. Alnabari and S. Bittner. Synthesis, 2000, 8, 1087–1090.

  18. SADABS, v. 2008-1. Bruker AXS: Madison, WI, USA, 2008.

  19. G. M. Sheldrick. Acta Crystallogr., Sect. C, 2015, 71, 3–8.

  20. A. L. Spek. J. Appl. Crystallogr., 2003, 36, 7–13.

  21. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. van de Stree. J. Appl. Crystallogr., 2006, 39, 453–457.

  22. H.-J. Kallmayer and B. Thierfelder. Pharmazie, 2002, 57, 456–459.

  23. D. Buckley, H. B. Henbest, and P. Slade. J. Chem. Soc., 1957, 4891–4900.

  24. E. P. Fokin, E. P. Prudchenko, and Yu. T. Glushkov. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1970, 3, 123–125.

  25. F. H. Allen, O. Kenard, D. G. Watson, L. Bramer, A. G. Orpen, and R. Taylor. J. Chem. Soc., Perkin Trans2, 1987, S1–S19.

  26. G. V. Noshchenko, N. F. Salivon, B. Zarychta, and V. V. Olijnyk. J. Struct. Chem., 2013, 54(1), 136–140.

  27. A. Krivokapic and H. L. Anderson. Acta Crystallogr., Sect. E, 2002, 58, o259–o260.

  28. N. Batenko, O. Popova, S. Belyakov, and R. Valters. Chem. Heterocycl. Compd., 2012, 48(6), 955–959.

  29. T. V. Rybalova and I. Yu. Bagryanskaya. J. Struct. Chem., 2009, 50(4), 767–779.

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Funding

The study was supported by the Russian Science Foundation (project No. 17-73-10238).

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Correspondence to S. I. Zhivetyeva.

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Zhivetyeva, S.I., Zayakin, I.A., Bagryanskaya, I.Y. et al. 2-DIETHYLAMINOVINYL DERIVATIVES OF HALOGENATED 1,4-QUINONES: SYNTHETIC AND STRUCTURAL ASPECTS. J Struct Chem 61, 1253–1259 (2020). https://doi.org/10.1134/S0022476620080107

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  • DOI: https://doi.org/10.1134/S0022476620080107

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