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Clay-catalysed radical addition of aliphatic thiols to styrene

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Abstract

When placed in K10-montmorillonite and cation-exchanged clays, alkanethiols undergo facile anti-Markovnikov addition to styrene by way of a radical mechanism forming sulfides. Surfactant pillared clays are found to be remarkably selective by suppressing side reactions.

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References

  1. (a) J.M. Adams, S.E. Davies, S.H. Graham and J.M. Thomas, J. Catal. 78 (1982) 197; (b) J.A. Ballantine, J.H. Purnell and J.M. Thomas, Clay Mineral. 18 1983) 347; (c) J.M. Adams, D.E. Clement and S.H. Graham, Clays Clay Miner. 30 1982) 129.

    Article  CAS  Google Scholar 

  2. (a) P. Laszlo, Science 235 (1987) 1473; (b) T.J. Pinnavia, Science 220 (1983) 4595.

    CAS  Google Scholar 

  3. (a) J.A. Ballantine, M. Davies, H. Purnell, M. Rayanakorn, J.M. Thomas and K.J. Williams, J. Chem. Soc. Chem. Commun. (1981) 8; (b)R. Burch and C.I. Warburton, J. Catal. 97 (1986) 511; (c) O. Sieskind and P. Albrecht, Tetrahedron Lett. 26 (1985) 2135.

  4. (a) J. Tateiwa, H. Horiuchi, K. Hashimoto, T. Yamauchi and S. Uemura, J.Org. Chem. 59 (1994) 5901; (b) M. Hirano, Y. Ueno and T. Morimoto, Synth. Commun. 25 (1995) 3125; (c) K. Higuchi, M. Onaka and Y. Izumi, Bull. Chem. Soc. Jpn. 66 (1993) 2016.

    Article  CAS  Google Scholar 

  5. (a) D. Kotkar and P.K. Ghosh, J. Chem. Soc. Chem. Commun. (1986) 650; (b) J. Cabral, P. Laszlo and M.T. Montaufier, Tetrahedron Lett. 29 (1988) 547; (c) C.G. Bruce, in: Materials Chemistry (1995) p. 301.

  6. (a) K. Pitchumani and A. Pandian, J. Chem. Soc. Chem. Commun. (1990) 1613; (b) K. Pitchumani, P. Baskar and C. Venkatachalaphathy, Catal. Lett. 21 (1993) 157; (c) P. Kannan, K. Pitchumani, S. Rajagopal and C. Srinivasan, J. Chem. Soc. Chem. Commun. (1996) 369.

  7. UK patent 625646 (1949);CA44, 5377d (1950); US patent 3083231 (1963);CA59, 8596c (1963); Belgium patent 886261 (1981);CA96, 51802c (1982).

  8. A. Cornelis and P. Laszlo, Synthesis (1985) 909.

  9. O. Ito, J. Org. Chem. 58 (1993) 1466.

    Article  CAS  Google Scholar 

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Authors
  1. P. Kannan
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  2. K. Pitchumani
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Kannan, P., Pitchumani, K. Clay-catalysed radical addition of aliphatic thiols to styrene. Catalysis Letters 45, 271–273 (1997). https://doi.org/10.1023/A:1019023830440

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