Regioselective methanesulfonylation of toluene catalysed by cation-exchanged zeolite β

Abstract

The reaction of methanesulfonic anhydride with toluene over various cation exchanged zeolite beta catalysts affords higher para-selectivity and better yields of methyl tolyl sulfone than standard Friedel–Crafts sulfonylation utilising aluminium chloride.

References

1. K. Smith and K. Fry, Tetrahedron Lett., 1989, 30, 5333.
2. K. Smith, M. Butters and B. Nay, Synthesis, 1985, 1157.
3. K. Smith, A. Musson and G. A. DeBoos, Chem. Commun., 1996, 469.
4. K. Smith and D. Bahzad, Chem. Commun., 1996, 467.
5. R. Q. Kluttz and L. H. Slaugh, US Pat 4 395 372, 1983(Chem Abstr., 1983, 99, P139469x).
6. A. Corma, H. Garcia and J. Primo, J. Chem. Res. (S.), 1988, 40.
7. P. Geneste, B. Chiche, A. Finiels and C. Gauthier, J. Org. Chem., 1986, 51, 2128.
8. H. A. Bouncer, Eur. Pat. 160144, 1985(Chem. Abstr., 1986, 104, P148457r).
9. A. Cornélis and P. Laszlo, Synthesis, 1985, 909.
10. P. Laszlo, Chem. Ind. (London), 1994, 53, 429.
11. G. A. Olah, S. Kobayashi and J. Nishimura, J. Am. Chem. Soc., 1973, 95, 564.
12. Publicity document on Envirocats, Contract Catalysts plc.
13. S. Daley, K. A. Trevor, K. R. Randles and B. D. Gott, PTC Int. Appl. WO93 18.000, 1993(Chem. Abstr., 1994, 120, P54320u).