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Lignin-type, α,β-unsaturated aldehydes of lignin-type in organic solvents

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An Erratum to this article was published on 01 June 2012

Abstract

A 1:1 reaction of [HO(CH2)3]3P with 4-hydroxy-3-methoxy-cinnamaldehyde (coniferaldehyde) or 3,5-dimethoxy-4-hydroxycinnamaldehyde (sinapaldehyde) in acetone at room temperature affords phosphonium zwitterions of the type R3P+CH(4-O−-Ar)CH2CHO; other phosphines [R = Et, n-Bu, (CH2)2CN, and p-Tol] do not react under the same conditions. In alcohols R’OH(D) [R’ = CD3, Et, (CD3)2CD, s-Bu, HOCH2CH2], the above phosphines (except the cyano-derivative) and those where R = i-Pr, Cy, Me2Ph, MePh2 do react within an equilibrium established between the reactants and the zwitterion-hemiacetal products R3P+CH(4-O−-Ar)CH2CH(OH)(OR′) that are formed as a mixture of two diastereomers. The nature of the phosphine and the alcohol affects the equilibrium and the diastereomeric ratio.

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References

  1. Hu, T.Q., James, B.R., Yawalata, D., and Ezhova, M.B., J. Pulp Paper Sci., 2004, vol. 30, no 8, p. 233.

    Google Scholar 

  2. Hu, T.Q., James, B.R., Yawalata, D., and Ezhova, M.B., World Patent (PCT WO 2004 070110 A1), 2004.

  3. Hu, T.Q., James, B.R., Yawalata, D., and Ezhova, M.B., J. Pulp Paper Sci., 2006, vol. 32, no. 3, p. 131.

    CAS  Google Scholar 

  4. Chandra, R., Hu, T.Q., James, B.R., Ezhova, M.B., and Moiseev, D.V., J. Pulp Paper Sci., 2007, vol. 33, no. 1, p. 15.

    CAS  Google Scholar 

  5. Joó, F., Aqueous Organometallic Catalysis, Dordrecht: Kluwer Academic Publishers, 2001.

    Google Scholar 

  6. Cole-Hamilton, D. and Tooze, R., Catalyst Separation, Recovery and Recycling, Dordrecht: Springer, 2006.

    Book  Google Scholar 

  7. James, B.R. and Lorenzini, F., Coord. Chem. Rev., 2010, vol. 254. nos. 5–6, p. 420.

    Article  Google Scholar 

  8. Moiseev, D.V., James, B.R., and Hu, T.Q., Inorg. Chem., 2006, vol. 45, no. 25, p. 10338.

    Article  CAS  Google Scholar 

  9. Moiseev, D.V., Patrick, B.O., and James, B.R., Inorg. Chem., 2009, vol. 48, no. 1, p. 239.

    Article  CAS  Google Scholar 

  10. Moiseev, D.V., James, B.R., Patrick, B.O., and Hu, T.Q., Inorg. Chim. Acta, 2010, vol. 363, No. 13, p. 3569.

    Article  CAS  Google Scholar 

  11. Moiseev, D.V., James, B.R., and Hu, T.Q., Inorg. Chem., 2007, vol. 46, no. 11, p. 4704.

    Article  CAS  Google Scholar 

  12. Moiseev, D.V., James, B.R., Patrick, B.O., and Hu, T.Q., Inorg. Chem., 2007, vol. 46, no. 22, p. 9389.

    Article  CAS  Google Scholar 

  13. Moiseev, D.V. and James, B.R., Can. J. Chem., 2009, vol. 87, no. 4, p. 582.

    Article  CAS  Google Scholar 

  14. Moiseev, D.V., Patrick, B.O., and James, B.R., Inorg. Chem., 2007, vol. 46, no. 26, p. 11467.

    Article  CAS  Google Scholar 

  15. Carlone, A., Bartoli, G., Bosco, M., Sambri, L., and Melchiorre, P., Angew. Chem. Int. Ed., 2007, vol. 46, no. 24, p. 4504.

    Article  CAS  Google Scholar 

  16. Ibrahem, I., Rios, R., Vesley, J., Hammar, P., Eriksson, L., Himo, F., and Córdova, A., Angew. Chem. Int. Ed., 2007, vol. 46, no. 24, p. 4507.

    Article  CAS  Google Scholar 

  17. Tolman, C.A., Chem. Rev., 1977, vol. 77, no. 3, p. 313.

    Article  CAS  Google Scholar 

  18. Henderson, W.A. and Buckler, S.A., J. Am. Chem. Soc., 1960, vol. 82, no. 22, p. 5794.

    Article  CAS  Google Scholar 

  19. Galkin, V.I., Salin, A.V., Bakhtiyarova Yu.V., and Sobanov, A.A., Russ. J. Gen. Chem., 2009, vol. 79, no. 5, p. 919.

    Article  CAS  Google Scholar 

  20. Salin, A.V., Sobanov, A.A., Bakhtiyarova, Yu.V., Khabibullin, A.A., and Galkin, V.I., Russ. J. Gen. Chem., 2010, vol. 80, no. 9, p. 1738.

    Article  CAS  Google Scholar 

  21. Smith, M.B. and March, J., Advanced Organic Chemistry, New York: Wiley Interscience, 2001 p. 1218.

    Google Scholar 

  22. Vullo, W.J., Ind. Eng. Chem. Prod. Res. Dev., 1966, vol. 5, no. 4, p. 346.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of British Columbia, Vancouver, British Columbia, Canada, V6T 1Z1

    D. V. Moiseev & B. R. James

  2. Department of Organic Chemistry, Lobachevskii Nizhny Novgorod State University, pr. Gagarina 23, Nizhny Novgorod, 603950, Russia

    D. V. Moiseev & A. V. Gushchin

Authors
  1. D. V. Moiseev
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  2. B. R. James
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  3. A. V. Gushchin
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Correspondence to D. V. Moiseev.

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Original Russian Text © D.V. Moiseev, B.R. James, A.V. Gushchin, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 5, pp. 732–740.

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Moiseev, D.V., James, B.R. & Gushchin, A.V. Lignin-type, α,β-unsaturated aldehydes of lignin-type in organic solvents. Russ J Gen Chem 82, 840–847 (2012). https://doi.org/10.1134/S1070363212050064

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  • DOI: https://doi.org/10.1134/S1070363212050064

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