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Reactions of Unsaturated Ketones with Bis(trimethylsilyl) Hypophosphite

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Abstract

Bis(trimethylsilyl) hypophosphite reacts with unsaturated ketones (methyl vinyl ketone and mesityl oxide) to give, depending on the reaction conditions, 1: 1 or 1: 2 adducts after hydrolysis. It was found that the intramolecular cyclization of the 1: 2 reaction product with mesityl oxide, trimethylsilyl bis(2-methyl-4- oxopentan-2-yl)phosphinate, yields, after hydrolysis, a phosphorinane with exocyclic carbonyl and hydroxyl groups.

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References

  1. Horsman, G.P. and Zechel, D.L., Chem. Rev., 2017, vol. 117, no. 8, p. 5704. doi 10.1021/acs.chemrev.6b00536

    Article  CAS  Google Scholar 

  2. Vizel’, A.O. and Garaev, R.S., Novyi aspekt farmakologicheskogo podkhoda k soedineniyam fosfora. Dimefosfon (A New Aspect of the Pharmacological Approach to Phosphorus Compounds. Dimephosphon), Kazan: Pechat’-Servis-XXI Vek, 2011.

    Google Scholar 

  3. Malyshev, V.G. and Fedoskin, I.V., Primenenie dimefosfona v meditsine (farmakoliticheskie, patogeneticheskie i klinicheskie aspekty) [Application of Dimephosphon in Medicine (Pharmacolitic, Pathogenetic, and Clinical Aspects], Moscow: Nauka, 2008.

    Google Scholar 

  4. Mironov, V.F., Buzykin, B.I., Garaev, R.S., Tatarinov, D.A., Kashapov, L.R., Chestnova, R.V., Nabiullin, V.N., Il’yasov, A.V., and Zobov, V.V., Russ. Chem. Bull., 2014, vol. 63, no. 9, p. 2114. doi 10.1007/s11172-014-0708-2

    Article  CAS  Google Scholar 

  5. Yudelevich, V.I., Sokolov, L.B., and Ionin, B.I., Russ. Chem. Rev., 1980, vol. 49, no. 1, p. 46. doi 10.1070/RC1980v049n01ABEH002444

    Article  Google Scholar 

  6. Boyd, A.E. and Regan, A.C., Tetrahedron Lett., 1992, vol. 33, no. 6, p. 813. doi 10.1016/S0040-4039(00)77722-7

    Article  CAS  Google Scholar 

  7. Kurdyumova, N.R., Rozhko, L.F., Ragulin, V.V., and Tsvetkov, E.N., Russ. J. Gen. Chem., 1997, vol. 67, no. 12, p. 1852.

    CAS  Google Scholar 

  8. Tatarinov, D.A., Kostin, A.A., Baronova, T.A., Dobrynin, A.B., Mironova, E.V., Krivolapov, D.B., Buzykin, B.I., and Mironov, V.F., Russ. J. Org. Chem., 2013, vol. 49, no. 4, p. 516. doi 10.1134/S1070428013040040

    Article  CAS  Google Scholar 

  9. Mukaiyama, T., Org. React., 2005, vol. 28, no. 3, p. 203. doi 10.1002/0471264180.or028.03

    Google Scholar 

  10. Chintareddy, V.R., Wadhwa, K., and Verkade, J.G., J. Org. Chem., 2009, vol. 74, no. 21, p. 8118. doi 10.1021/jo901571y

    Article  CAS  Google Scholar 

  11. Flowers, R.A., Xu, X., Timmons, C., and Li, G., Eur. J. Org. Chem., 2004, vol. 2004, no. 14, p. 2988. doi 10.1002/ejoc.200400228

    Article  Google Scholar 

  12. Sheldrick, G.M., SADABS, Madison, Wis, USA: Bruker AXS, 1997.

    Google Scholar 

  13. Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr., Sect. A, 1991, vol. 47, p. 744. doi 10.1107/S0108767391006566

    Article  Google Scholar 

  14. Sheldrick, G.M., SHELX-97, Programs for Crystal Structure Analysis (Release 97-2), Göttingen: Univ. of Göttingen, 1997, vols. 1 and 2.

    Google Scholar 

  15. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. doi 10.1107/S0021889899006020

    Article  CAS  Google Scholar 

  16. APEX2 (Version 2.1), SAINT Plus. Data Reduction and Correction Program (Version 7.31A), Madison, Wis, USA: Bruker AXS, 2006.

    Google Scholar 

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Authors and Affiliations

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

    D. A. Tatarinov, A. B. Dobrynin & V. F. Mironov

  2. Kazan (Volga Region) Federal University, Kazan, Tatarstan, Russia

    D. A. Tatarinov, M. V. Kundina & V. F. Mironov

Authors
  1. D. A. Tatarinov
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  2. M. V. Kundina
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  3. A. B. Dobrynin
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  4. V. F. Mironov
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Correspondence to D. A. Tatarinov.

Additional information

Original Russian Text © D.A. Tatarinov, M.V. Kundina, A.B. Dobrynin, V.F. Mironov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 1, pp. 95–100.

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Tatarinov, D.A., Kundina, M.V., Dobrynin, A.B. et al. Reactions of Unsaturated Ketones with Bis(trimethylsilyl) Hypophosphite. Russ J Gen Chem 88, 90–95 (2018). https://doi.org/10.1134/S1070363218010140

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  • DOI: https://doi.org/10.1134/S1070363218010140

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