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Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides

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Abstract

Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides on heating with solid potassium hydroxide afforded the corresponding 1-(organylsulfanyl)propynes in moderate to high yields and minor isomeric allene derivatives, organylsulfanylpropadienes.

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References

  1. Radchenko, S.I. and Petrov, A.A., Russ. Chem. Rev., 1989, vol. 58, p. 948.

    Article  Google Scholar 

  2. Gleiter, R. and Werz, D.B., Chem. Rev., 2010, vol. 110, p. 4447.

    Article  CAS  Google Scholar 

  3. Poluchenie i svoistva organicheskikh soedinenii sery (Synthesis and Properties of Organic Sulfur Compounds), Belen’kii, L.I., Ed., Moscow: Khimiya, 1998.

  4. Manarin, F., Roehrs, J.A., Gay, R.M., Brandão, R., Menezes, P.H., Nogueira, C.W., and Zeni, G., J. Org. Chem., 2009, vol. 74, p. 2153.

    Article  CAS  Google Scholar 

  5. Chandanshive, J.Z., Bonini, B.F., Gentili, D., Fochi, M., Bernardi, L., and Franchini, M.C., Eur. J. Org. Chem., 2010, p. 6440.

    Google Scholar 

  6. Dabdoub, M.J., Dabdoub, V.B., and Pereira, M.A., Tetrahedron Lett., 2001, vol. 42, p. 1595.

    Article  CAS  Google Scholar 

  7. Zheng, W., Hong, Y., Wang, P., Zheng, F., Zhang, Y., and Wang, W., Tetrahedron Lett., 2013, vol. 54, p. 3643.

    Article  CAS  Google Scholar 

  8. Motto, J.M., Castillo, A., Greer, A., Montemayer, L.K., Sheepwash, E.E., and Schwan, A.L., Tetrahedron, 2011, vol. 67, p. 1002.

    Article  CAS  Google Scholar 

  9. Zaburdaeva, E.A. and Dodonov, V.A., Russ. Chem. Bull., Int. Ed., 2011, vol. 60, p. 185.

    Article  CAS  Google Scholar 

  10. Benisch, C., Gleiter, R., Staeb, T.H., Nuber, B., Oeser, T., Pritzkow, H., and Rominger, F., J. Organomet. Chem., 2002, vol. 641, p. 102.

    Article  CAS  Google Scholar 

  11. Fressigné, C., Lhermet, R., Girard, A.-L., Durandetti, M., and Maddaluno, J., J. Org. Chem., 2013, vol. 78, p. 9659.

    Article  Google Scholar 

  12. Magriotis, P.A. and Brown, J.T., Org. Synth., 1995, vol. 72, p. 252.

    Article  CAS  Google Scholar 

  13. Arens, J.F., Volger, H.C., and Doornobos, T., Recl. Trav. Chim. Pays–Bas, 1956, vol. 75, p. 1459.

    Article  CAS  Google Scholar 

  14. Brandsma, L. and Arens, J.F., Recl. Trav. Chim. Pays–Bas, 1961, vol. 80, p. 241.

    Article  CAS  Google Scholar 

  15. Brandsma, L. and Arens, J.F., Recl. Trav. Chim. Pays–Bas, 1962, vol. 81, p. 510.

    Article  CAS  Google Scholar 

  16. Levanova, E.P., Vakhrina, V.S., Grabel’nykh, V.A., Rozentsveig, I.B., Russavskaya, N.V., Albanov, A.I., Sanzheeva, E.R., and Korchevin, N.A., Russ. J. Org. Chem., 2015, vol. 51, p. 161.

    Article  CAS  Google Scholar 

  17. Levanova, E.P., Vakhrina, V.S., Grabel’nykh, V.A., Rozentsveig, I.B., Russavskaya, N.V., Albanov, A.I., and Korchevin, N.A., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, p. 1722.

    Article  CAS  Google Scholar 

  18. Levanova, E.P., Grabel’nykh, V.A., Vakhrina, V.S., Russavskaya, N.V., Albanov, A.I., Rozentsveig, I.B., and Korchevin N.A., Russ. J. Gen. Chem., 2014, vol. 84, p. 439.

    Article  CAS  Google Scholar 

  19. Brandsma, L., Wijers, H.E., and Jonker, M.C., Recl. Trav. Chim. Pays–Bas, 1964, vol. 83, p. 208.

    Article  CAS  Google Scholar 

  20. Levanova, E.P., Grabel’nykh, V.A., Elaev, A.V., Russavskaya, N.V., Klyba, L.V., Albanov, A.I., Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen. Chem., 2013, vol. 83, p. 1660.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    I. B. Rozentsveig, V. S. Nikonova, E. P. Levanova & N. A. Korchevin

Authors
  1. I. B. Rozentsveig
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  2. V. S. Nikonova
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  3. E. P. Levanova
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  4. N. A. Korchevin
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Corresponding author

Correspondence to I. B. Rozentsveig.

Additional information

Original Russian Text © I.B. Rozentsveig, V.S. Nikonova, E.P. Levanova, N.A. Korchevin, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1376–1378.

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Rozentsveig, I.B., Nikonova, V.S., Levanova, E.P. et al. Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides. Russ J Org Chem 52, 1264–1266 (2016). https://doi.org/10.1134/S1070428016090025

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  • DOI: https://doi.org/10.1134/S1070428016090025

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