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Caged phosphorane with P-C bond based on chloral and 4,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane

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Abstract

The key methods of caged phosphoranes synthesis are analyzed. Reaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane (prepared from the meso-form of 2,3-butanediol) with chloral has yielded the caged phosphorane containing a phosphorus-carbon bond: 1,1-(1,2-dimethylethylenedioxy)-3,4-diphenyl-6-trichloromethyl-2,5,7,1-trioxaphosphabicyclo[2.2.11,4]heptane; spatial structure of the product has been elucidated with X-ray diffraction analysis.

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References

  1. Eymery, F., Iorga, B., and Savignac, P., Tetrahedron, 1999, vol. 55, no. 46, p. 13109. DOI: 10.1016/S0040-4020(99)00822-4.

    Article  CAS  Google Scholar 

  2. Chemistry of Hypervalent Compounds, Akiba, K.-Y., Ed., New York: Wiley-VCH, 1999.

    Google Scholar 

  3. Kellerman, D.L., York, D.M., Piccirilli, J.A., and Harris, M.E., Curr. Opin. Chem. Biol., 2014, vol. 21, p. 96. DOI: 10.1016/j.cbpa.2014.06.010.

    Article  CAS  Google Scholar 

  4. Allen, K.N., and Dunaway-Mariano, D., Trends Biochem. Sci., 2004, vol. 29, no. 9, p. 495. DOI: 10.1016/j.tibs.2004.07.008.

    Article  CAS  Google Scholar 

  5. Turk, B.E., Curr. Opin. Chem. Biol., 2008, vol. 12, no. 1, p. 4. DOI: 10.1016/j.cbpa.2008.01.018.

    Article  CAS  Google Scholar 

  6. Swamy, K.C.K., and Kumar, N.S., Acc. Chem. Res., 2006, vol. 39, no. 5, p. 324. DOI: 10.1021/ar050188x.

    Article  CAS  Google Scholar 

  7. Kobayashi, J., and Kawashima, T., Comp. Rend. Chim., 2010, vol. 13, nos. 8–9, p. 1249. DOI: 10.1016/j.crci.2010.06.010.

    Article  CAS  Google Scholar 

  8. Marchi, C., and Buono, G., Tetrahedron Lett., 1999, vol. 40, no. 52, p. 9251. DOI: 10.1016/S0040-4039(99) 02023-7.

    Article  CAS  Google Scholar 

  9. Marchi, C., and Buono, G., Tetrahedron Lett., 2000, vol. 41, no. 17, p. 3073. DOI: 10.1016/S0040-4039(00) 00338-5.

    Article  CAS  Google Scholar 

  10. Marchi, C., and Buono, G., Inorg. Chem., 2000, vol. 39, no. 13, p. 2951. DOI: 10.1021/ic0000101.

    Article  CAS  Google Scholar 

  11. Duff, E., Trippett, S., and Whittle, P.J., J. Chem. Soc., Perkin Trans. 1, 1973, no. 9, p. 972. DOI: 10.1039/P19730000972.

    Google Scholar 

  12. Tarasova, R.I., Sinitsyna, N.I., Dvoinishnikova, T.A., and Moskva V.V., Zh. Obshch. Khim., 1983, vol. 53, no. 3, p. 694.

    CAS  Google Scholar 

  13. Tarasova, R.I., Sinitsyna, N.I., Dvoinishnikova, T.A., Remizov, A.B., Alparova, M.V., Zykova, T.V., and Moskva, V.V., Zh. Obshch. Khim., 1984, vol. 54, no. 7, p. 1489.

    CAS  Google Scholar 

  14. Pudovik, A.N., Konovalova, I.V., and Burnaeva, L.A., Synthesis, 1986, no. 10, p. 793. DOI: 10.1055/s-1986-31785.

    Google Scholar 

  15. Francke, R., Sheldrick, W.S., and Roschenthaler, G.-V., Chem. Ber., 1989, vol. 122, no. 2, p. 301. DOI: 10.1002/cber.19891220216.

    Article  CAS  Google Scholar 

  16. Konovalova, I.V., Burnaeva, L.A., Mironov, V.F., Khlopushina, G.A., and Pudovik, A.N., Zh. Obshch. Khim., 1994, vol. 64, no. 1, p. 63.

    CAS  Google Scholar 

  17. Hund, R.D., and Röschenthaler, G.V., Phosphorus, Sulfur, Silicon, Relat. Elem., 1991, vol. 62, nos. 1–4, p. 65. DOI: 10.1080/10426509108034459.

    Article  CAS  Google Scholar 

  18. Schoth, R.-M., Sevenard, D., Pashkevich, K., and Röschenthaler, G.-V., Coord. Chem. Rev., 2000, vol. 210, no. 1, p. 101. DOI:10.1016/S0010-8545(00) 00318-0.

    Article  CAS  Google Scholar 

  19. Vollbrecht, S., Vollbrecht, A., Jeske, J., Jones, P.G., Schmutzler, R., and Du Mont, W.W., Chem. Ber., 1997, vol. 130, no. 6, p. 819. DOI: 10.1002/cber.19971300623.

    Article  CAS  Google Scholar 

  20. Roesky, H.W., Pogatzki, V.W., Dhathathreyan, K.S., Thiel, A., Schmidt, H.G., Dyrbusch, M., Noltemeyer, M., and Sheldrick, G.M., Chem. Ber., 1986, vol. 119, no. 9, p. 2687. DOI: 10.1002/cber. 19861190903.

    Article  CAS  Google Scholar 

  21. Konovalova, I.V., Yarkova, E.G., Burnaeva, L.A., Khafizova, G.S., Khusnutdinova, E.K., Il’ina, L.F., and Pudovik, A.N., Zh. Obshch. Khim., 1988, vol. 58, no. 5, p. 989.

    CAS  Google Scholar 

  22. Aly, H.A.E., Barlow, J.H., Russell, D.R., Smith, D.J.H., Swindles, M., and Trippett, S., J. Chem. Soc. Chem. Commun., 1976, no. 12, p. 449. DOI: 10.1039/C39760000449.

    Google Scholar 

  23. Konovalova, I.V., Dokuchaeva, I.S., Trishin, Yu.G., Burnaeva, L.A., Chistokletov, V.N., and Pudovik, A.N., Zh. Obshch. Khim., 1989, vol. 59, no. 8, p. 1726.

    CAS  Google Scholar 

  24. Konovalova, I.V., Trishin, Yu.G., Dokuchaeva, I.S., Burnaeva, L.A., Efremov, Yu.Ya., Kazanina, T.Yu., Chistokletov, V.N., and Pudovik, A.N., Zh. Obshch. Khim., 1990, vol. 60, no. 8, p. 1706.

    CAS  Google Scholar 

  25. Burangulova, R.N., Trishin, Yu.G., Konovalova, I.V., Burnaeva, L.A., Chistokletov, V.N., and Pudovik, A.N., Zh. Obshch. Khim., 1989, vol. 59, no. 9, p. 1979.

    CAS  Google Scholar 

  26. Trishin, Yu.G., Konovalova, I.V., Burangulova, R.N., Burnaeva, L.A., Chistokletov, V.N., and Pudovik, A.N., Zh. Obshch. Khim., 1988, vol. 58, no. 11, p. 2434.

    CAS  Google Scholar 

  27. Trishin, Yu.G., Konovalova, I.V., Burangulova, R.N., Burnaeva, L.A., Chistokletov, V.N., and Pudovik, A.N., Tetrahedron Lett., 1989, vol. 30, no. 5, p. 577. DOI: 10.1016/S0040-4039(00)95259-6.

    Article  CAS  Google Scholar 

  28. Huang, Y., Arif, A.M., and Bentrude, W.G., J. Am. Chem. Soc., 1991, vol. 113, no. 20, p. 7800. DOI: 10.1021/ja00020a073.

    Article  CAS  Google Scholar 

  29. Huang, Y., Sopchik, A.E., Arif, A.M., and Bentrude, W.G., J. Am. Chem. Soc., 1993, vol. 115, no. 10, p. 4031. DOI: 10.1021/ja00063a024.

    Article  CAS  Google Scholar 

  30. Huang, Y., Arif, A.M., and Bentrude, W.G., Phosphorus, Sulfur, Silicon, Relat. Elem., 1995, vol. 103, nos. 1–4, p. 225. DOI: 10.1080/10426509508027381.

    Article  CAS  Google Scholar 

  31. Trishin, Yu.G., Burnaeva, L.A., Khusnutdinova, E.K., Chistokletov, V.N., and Pudovik, A.N., Zh. Obshch. Khim., 1988, vol. 58, no. 6, p. 1292.

    Google Scholar 

  32. Huang, Y., Arif, A.M., and Bentrude, W.G., J. Am. Chem. Soc., 1991, vol. 113, no. 20, p. 7800. DOI: 10.1021/ja00020a073.

    Article  CAS  Google Scholar 

  33. Schmidpeter, A., Schomburg, D., Sheldrick, W.S., and Weinmaier, J.H., Angew. Chem. Int. Ed., 1976, vol. 15, no. 12, p. 781. DOI: 10.1002/anie.197607811.

    Article  Google Scholar 

  34. Schmidpeter, A., and Weinmaier, J.H., Z. Naturforsch. B, 1979, vol. 34, no. 7, p. 906.

    Google Scholar 

  35. Schmidpeter, A., and Weinmaier, J.H., Angew. Chem. Int. Ed., 1975, vol. 14, no. 7, p. 489. DOI: 10.1002/anie.197504891.

    Article  Google Scholar 

  36. Sheldrick, W.S., Schmidpeter, A., and Weinmaier, J.H.Z., Angew. Chem. Int. Ed., 1975, vol. 14, no. 7, p. 490. DOI: 10.1002/anie.197504901.

    Article  Google Scholar 

  37. Harper, S.D., and Arduengo, A.J., J. Am. Chem. Soc., 1982, vol. 104, no. 9, p. 2497. DOI: 10.1021/ja00373a027.

    Article  CAS  Google Scholar 

  38. Mukhametov, F.S., and Korshin, E.E., Izv. Akad. Nauk USSR. Ser. Khim., 1985, no. 2, p. 493; Mukhametov, F.S., and Korshin, E.E., Bull. Acad. Sci. USSR. Div. Chem. Sci., 1985, vol. 34, no. 2, p. 451. DOI: 10.1007/BF00951316.

    Google Scholar 

  39. Dahlhoff, W.V., Taba, K.M., and Mynott, R., Z. Naturforsch. B, 1989, vol. 44, no. 1, p. 41.

    Article  CAS  Google Scholar 

  40. Bekiaris, G., and Röschenthaler, G.-V., Z. Naturforsch. B, 1990, vol. 45, no. 10, p. 1460.

    Article  CAS  Google Scholar 

  41. Hund, R.D., Behrens, U., and Röschenthaler, G.-V., Phosphorus, Sulfur, Silicon, 1992, vol. 69, nos. 1–2, p. 119. DOI: 10.1080/10426509208036860.

    Article  Google Scholar 

  42. Bekiaris, G., and Röschenthaler, G.-V., Heteroatom. Chem., 1998, vol. 9, no. 2, p. 173. DOI: 10.1002/(SICI) 1098-1071(1998)9:2〈173::AID-HC13〉3.0.CO;2-O.

    Article  CAS  Google Scholar 

  43. Abdrakhmanova, L.M., Mironov, V.F., Baronova, T.A., Dimukhametov, M.N., Krivolapov, D.B., Litvinov, I.A., Balandina, A.A., Latypov, Sh.K., and Konovalov, A.I., Mendeleev Commun., 2006, vol. 16, no. 6, p. 320. DOI: 10.1070/MC2006v016n06ABEH00 2414.

    Article  Google Scholar 

  44. Abdrakhmanova, L.M., Mironov, V.F., Gryaznova, T.P., Katsyuba, S.A., and Dimukhametov, M.N., Phosphorus, Sulfur, Silicon, Relat. Elem., 2011, vol. 186, no. 4, p. 652. DOI: 10.1080/10426507.2010.521434.

    Article  CAS  Google Scholar 

  45. Dimukhametov, M.N., Mironov, V.F., Krivolapov, D.B., Mironova, E.V., and Musin, R.Z., Russ. Chem. Bull. Int. Ed., 2013, vol. 62, no. 4, p. 1091. DOI: 10.1007/s11172-013-0147-5.

    Article  CAS  Google Scholar 

  46. Konovalova, I.V., Ofitserov, E.N., Sinyashina, T.N., Mironov, V.F., and Pudovik, A.N., Bull. Acad. Sci. USSR. Div. Chem. Sci., 1987, vol. 36, no. 5, p. 1078. DOI: 10.1007/BF00956378.

    Article  Google Scholar 

  47. Sheldrick, G.M., SADABS, Bruker AXS Inc., Madison, WI-53719, USA, 1997.

    Google Scholar 

  48. Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr. (A), 1991, vol. 47, no. 6, p. 744. DOI: 10.1107/S0108767391006566.

    Article  Google Scholar 

  49. Sheldrick, G.M., SHELX-97, Program for Crystal Structure Refinement, Göttingen, Germany, University of Göttingen. 1997, vol. 1, 2.

    Google Scholar 

  50. Farrugia, L.J., J. Appl. Crystal., 1999, vol. 32,pt. 4, p. 837. DOI: 10.1107/S0021889899006020.

    Article  CAS  Google Scholar 

  51. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advansed X-ray Solutions, BrukerAXS Inc., Madison, Wisconsin, USA, 2006.

  52. Spek, A.L., J. Appl. Cryst., 2003, vol. 36, no. 1, p. 7. DOI: 10.1107/S0021889802022112.

    Article  CAS  Google Scholar 

  53. Farrugia, L.J., J. Appl. Cryst., 1997, vol. 30,pt. 5, no. 1, p. 565. DOI: 10.1107/S0021889897003117.

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

    V. F. Mironov, M. N. Dimukhametov, E. V. Mironova, D. B. Krivolapov & L. M. Abdrakhmanova

  2. Kazan Federal University, Kazan, Tatarstan, Russia

    V. F. Mironov, E. V. Mironova & G. A. Ivkova

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  1. V. F. Mironov
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  2. M. N. Dimukhametov
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  3. E. V. Mironova
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  6. L. M. Abdrakhmanova
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Original Russian Text © V.F. Mironov, M.N. Dimukhametov, E.V. Mironova, D.B. Krivolapov, G.A. Ivkova, L.M. Abdrakhmanova, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 2, pp. 277–288.

To the 80th Anniversary of B.I. Ionin

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Mironov, V.F., Dimukhametov, M.N., Mironova, E.V. et al. Caged phosphorane with P-C bond based on chloral and 4,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane. Russ J Gen Chem 85, 450–461 (2015). https://doi.org/10.1134/S1070363215020164

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