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Reactions of Arylenedioxytrihalophosphoranes with Acetylenes: XV.1 Reaction of 2,2,2-Tribromo-4,6-di-tert-butylbenzo-1,3,2λ5-dioxaphospholedioxaphosphole with Pent-1-yne

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Abstract

2,2,2-Tribromo-4,6-di-tert-butylbenzo-1,3,2λ5-dioxaphospholedioxaphosphole reacted with a terminal alkyne, pent-1-yne, to give a mixture of two isomeric 1,2-benzoxaphosphinine derivatives, 6,8- and 5,7-di-tert-butyl-2-bromo-4-propylbenzo-1,2λ5-oxaphosphinin-2-oxides, at a ratio of 5.9: 1. The regioselectivity of substitution of oxygen in the dioxaphosphole fragment by carbon differs from that observed previously in the reaction with 4,6-di-tert-butyl-2,2,2-trichlorobenzo-1,3,2λ5-dioxaphosphole: the minor isomer was formed as a result of substitution of the oxygen atom in the ortho position with respect to one tert-butyl group of the initial phosphole.

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References

  1. Nemtarev, A.V., Mironov, V.F., Aniskin, A.S., Baranov, D.S., Krivolapov, D.B., Musin, R.Z., and Vasilevskii, S.F., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, no. 5, p. 1299. doi 10.1007/s11172-016-1452-6

    Article  CAS  Google Scholar 

  2. Coumarins: Biology, Applications, and Mode of Action, O’Kennedy, R. and Thornes, R.D., Eds., Chichester: Wiley, 1997.

  3. Yarnell, E. and Abascal, K., Altern. Complementary Ther., 2009, vol. 15, no. 1, p. 24. doi 10.1089/act.2009.15104

    Article  Google Scholar 

  4. Musa, M.A., Cooperwood, J.S., Khan, M., and Omar, F., Curr. Med. Chem., 2008, vol. 15, no. 26, p. 2664. doi 10.2174/092986708786242877

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Borges, F., Roleira, F., Milhazes, N., Santana, L., and Uriarte, E., Curr. Med. Chem., 2005, vol. 12, no. 8, p. 887. doi 10.2174/0929867053507315

    Article  CAS  PubMed  Google Scholar 

  6. Kostova, I., Curr. Med. Chem. Anti-Cancer Agents, 2005, vol. 5, no. 1, p. 29. doi 10.2174/1568011053352550

    Article  CAS  PubMed  Google Scholar 

  7. Kostova, I., Raleva, S., Genova, P., and Argirova, R., Biotechnol. Biotechnol. Equip., 2005, vol. 19, no. 1, p. 16. doi 10.1080/13102818.2005.10817148

    Article  CAS  Google Scholar 

  8. Coumarin Anticoagulant Research Progress, Edardes, J.P., Ed., New York: Nova Biomedical Books, 2008.

  9. Grazul, M. and Budzisz, E., Coord. Chem. Rev., 2009, vol. 253, nos. 21–22, p. 2588. doi 10.1016/j.ccr.2009.06.015

    Article  CAS  Google Scholar 

  10. Budzisz, E., Brzezinska, E., Krajewska, U., and Rozalski, M., Eur. J. Med. Chem., 2003, vol. 38, no. 6, p. 597. doi 10.1016/S0223-5234(03)00086-2

    Article  CAS  PubMed  Google Scholar 

  11. Li, X., Zhang, D., Pang, H., Shen, F., Fu, H., Jiang, Y., and Zhao, Y., Org. Lett., 2005, vol. 7, no. 22, p. 4919. doi 10.1021/ol051871m

    Article  CAS  PubMed  Google Scholar 

  12. Li, X., Wang, Y., Fu, H., Jiang, Y., and Zhao, Y., Bioorg. Chem., 2006, vol. 34, no. 2, p. 105. doi 10.1016/j.bioorg.2006.01.003

    Article  CAS  PubMed  Google Scholar 

  13. Bojilova, A., Nikolova, R., Ivanov, C., Rodios, N.A., Terzis, A., and Raptopoulou, C.P., Tetrahedron, 1996, vol. 52, no. 38, p. 12597. doi 10.1016/0040-4020(96) 00748-X

    Article  CAS  Google Scholar 

  14. Budzisz, E., Phosphorus, Sulfur Silicon Relat. Elem., 2004, vol. 179, no. 10, p. 2131. doi 10.1080/10426500490475139

    Article  CAS  Google Scholar 

  15. Sadikova, L.M., Sadykova, Y.M., Zalaltdinova, A.V., Burilov, A.R., Pudovik, M.A., Voronina, J.K., and Mitrasov, Y.N., Phosphorus, Sulfur Silicon Relat. Elem., 2016, vol. 191, nos. 11–12, p. 1562. doi 10.1080/10426507.2016.1213260

    Article  CAS  Google Scholar 

  16. Sadykova, Y.M., Sadikova, L.M., Badrtdinova, A.R., Dobrynin, A.B., Burilov, A.R., and Pudovik, M.A., Phosphorus, Sulfur Silicon Relat. Elem., 2015, vol. 190, no. 12, p. 2267. doi 10.1080/10426507.2015.1073283

    Article  CAS  Google Scholar 

  17. Hill, R.A., Macaulay, G.S., and MacLachlan, W.S., J. Chem. Soc., Perkin Trans. 1, 1987, no. 10, p. 2209. doi 10.1021/jo00437a025

    Article  Google Scholar 

  18. Budzisz, E. and Pastuszko, S., Tetrahedron, 1999, vol. 55, no. 15, p. 4815. doi 10.1016/S0040-4020(99) 00153-2

    Article  Google Scholar 

  19. Li, X., Shen, F., Jiang, Y., and Zhao, Y., Synlett, 2006, no. 4, p. 630. doi 10.1002/chin.200628165

    Google Scholar 

  20. Mironov, V.F. and Nemtarev, A.V., Rev. J. Chem., 2011, vol. 1, no. 1, p. 27. doi 10.1134/S2079978011010067

    Article  Google Scholar 

  21. Nemtarev, A.V., Varaksina, E.N., Mironov, V.F., Musin, R.Z., and Konovalov, A.I., Russ. J. Org. Chem., 2007, vol. 43, no. 3, p. 468. doi 10.1134/S107042800703027X

    Article  CAS  Google Scholar 

  22. Nemtarev, A.V., Mironov, V.F., Varaksina, E.N., Nelyubina, Y.V., Antipin, M.Yu., Musin, R.Z., and Konovalov, A.I., Mendeleev Commun., 2007, vol. 17, no. 1, p. 1. doi 10.1016/j.mencom.2007.11.009

    Article  CAS  Google Scholar 

  23. Aniskin, A.S., Nemtarev, A.V., Baranov, D.S., Mironov, V.F., and Vasilevskii, S.F., Russ. J. Gen. Chem., 2013, vol. 83, no. 5, p. 1010. doi 10.1134/S1070363213050253

    Article  CAS  Google Scholar 

  24. Nemtarev, A.V., Mironov, V.F., Aniskin, A.S., Baranov, D.S., Mironova, E.V., Krivolapov, D.B., Musin, R.Z., Vasilevskii, S.F., Druzhkov, N.O., and Cherkasov, V.K., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, no. 1, p. 55. doi 10.1007/s11172-013-0008-2

    Article  CAS  Google Scholar 

  25. Mironov, V.F., Nemtarev, A.V., Varaksina, E.N., Shtyrlina, A.A., Gubaidullin, A.T., Litvinov, I.A., and Dobrynin, A.B., Russ. J. Org. Chem., 2014, vol. 50, no. 6, p. 864. doi 10.1134/S1070428014060190

    Article  CAS  Google Scholar 

  26. Aniskin, A.S., Nemtarev, A.V., Baranov, D.S., Vasilevskii, S.F., and Mironov, V.F., Russ. J. Gen. Chem., 2015, vol. 85, no. 9, p. 2206. doi 10.1134/S1070363215090285

    Article  CAS  Google Scholar 

  27. Mironov, V.F., Gubaidullin, A.T., Petrov, R.R., Litvinov, I.A., Shtyrlina, A.A., Zyablikova, T.A., Azancheev, N.M., Konovalov, A.I., and Musin, R.Z., Phosphorus, Sulfur Silicon Relat. Elem., 1999, vols. 144–146, no. 1, p. 377. doi 10.1080/10426509908546260

    Article  Google Scholar 

  28. Nemtarev, A.V., Mironov, V.F., Varaksina, E.N., Gubaidullin, A.T., Krivolapov, D.B., Musin, R.Z., and Litvinov, I.A., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, no. 1, p. 149. doi 10.1007/s11172-014-0409-x

    Article  CAS  Google Scholar 

  29. Varaksina, E.N., Mironov, V.F., Nemtarev, A.V., Musin, R.Z., Balandina, A.A., Latypov, Sh.K., and Konovalov, A.I., Mendeleev Commun., 2006, vol. 16, no. 3, p. 172. doi 10.1070/MC2006v016n03ABEH002321

    Article  CAS  Google Scholar 

  30. Nemtarev, A.V., Varaksina, E.N., Mironov, V.F., Musin, R.Z., and Konovalov, A.I., Russ. J. Org. Chem., 2007, vol. 43, no. 11, p. 1737. doi 10.1134/S1070428007110280

    Article  CAS  Google Scholar 

  31. Mironov, V.F., Bogdanov, A.V., Nemtarev, A.V., Shtyrlina, A.A., Varaksina, E.N., Cherkasov, V.K., Dobrynin, A.B., Krivolapov, D.B., Musin, R.Z., Litvinov, I.A., and Konovalov, A.I., Russ. Chem. Bull., Int. Ed., 2007, vol. 56, no. 9, p. 1900. doi 10.1007/s11172-007-0292-9

    Article  CAS  Google Scholar 

  32. Nemtarev, A.V., Mironov, V.F., Bogdanov, A.V., Cherkasov, V.K., Druzhkov, N.O., Gubaidullin, A.T., Litvinov, I.A., and Musin, R.Z., Russ. Chem. Bull., Int. Ed., 2009, vol. 58, no. 1, p. 182. doi 10.1007/s11172-009-0028-0

    Article  CAS  Google Scholar 

  33. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2015, vol. 71, p. 3. doi 10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  34. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. doi 10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  35. Spek, A.L., Acta Crystallogr., Sect. D, 2009, vol. 65, p. 148. doi 0.1107/S090744490804362X

    Article  CAS  Google Scholar 

  36. Farrugia, L.J., J. Appl. Crystallogr., 2012, vol. 45, p. 849. doi 10.1107/S0021889812029111

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, Tatarstan, 420088, Russia

    A. V. Nemtarev, V. F. Mironov, R. R. Fayzullin, I. A. Litvinov & R. Z. Musin

  2. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008, Russia

    A. V. Nemtarev & V. F. Mironov

Authors
  1. A. V. Nemtarev
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  2. V. F. Mironov
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  3. R. R. Fayzullin
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  4. I. A. Litvinov
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  5. R. Z. Musin
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Correspondence to A. V. Nemtarev.

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Dedicated to the 115th anniversary of B.A. Arbuzov’s birth

Original Russian Text © A.V. Nemtarev, V.F. Mironov, R.R. Fayzullin, I.A. Litvinov, R.Z. Musin, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 11, pp. 1810–1816.

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Nemtarev, A.V., Mironov, V.F., Fayzullin, R.R. et al. Reactions of Arylenedioxytrihalophosphoranes with Acetylenes: XV.1 Reaction of 2,2,2-Tribromo-4,6-di-tert-butylbenzo-1,3,2λ5-dioxaphospholedioxaphosphole with Pent-1-yne. Russ J Gen Chem 88, 2290–2295 (2018). https://doi.org/10.1134/S1070363218110075

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