Mesityl methyl sulfone 10. Solid, mp 129 ЊC (lit.,6e 130 ЊC); IR
4 (a) P. D. Magnus, Tetrahedron, 1977, 33, 2019; (b) L. Field,
1
(KBr) 1126, 1295 cmϪ1; H NMR (200 MHz; CDCl3) δ 2.30
Synthesis, 1978, 713.
5 K. M. Roy, in Ullmann’s Encyclopedia of Industrial Chemistry,
ed. W. Gerhartz, VCH, Weinheim, Germany, 1985, vol. A25,
pp. 487–501.
(3 H, s, CH3), 2.64 (6 H, s, 2 × CH3), 3.0 (3 H, s, CH3), 6.93 (2
H, s).
6 (a) F. R. Jensen and G. Goldman, in Friedel–Crafts and Related
Reactions, ed. G. Olah, Wiley-Interscience, New York, 1964, vol. III,
pp. 1319–1367; (b) R. Taylor, in Comprehensive Chemical Kinetics,
ed. C. H. Bamford and C. F. H. Tipper, Elsevier, New York, 1972,
pp. 77–83; (c) G. A. Olah, S. Kobayashi and J. Nishimura, J. Am.
Chem. Soc., 1973, 95, 564; (d) G. A. Olah and H. C. Lin, Synthesis,
1974, 342; (e) J. A. Hyatt and A. W. White, Synthesis, 1984, 214;
( f) M. Desbois, US Pat., 4 554 381, 1985 (Chem. Abstr., 1985, 103,
P141625q); (g) F. Effenberger and K. Huthmacher, Angew.
Chem., Int. Ed. Engl., 1974, 13, 409; (h) S. Repichet, C. L. Roux,
P. Hernandez and J. Dubac, J. Org. Chem., 1999, 64, 6479.
7 (a) B. M. Graybill, J. Org. Chem., 1967, 32, 2931; (b) H. J. Sipe,
Jr., D. W. Clary and S. B. White, Synthesis, 1984, 283; (c) M. Ueda,
K. Uchiyama, T. Kano, Synthesis, 1984, 323.
Mesityl p-tolyl sulfone 11. Solid, mp 123 ЊC (lit.,7a 117 ЊC); IR
1
(KBr) 1155, 1310 cmϪ1; H NMR (200 MHz; CDCl3) δ 2.29
(3 H, s, CH3), 2.41 (3 H, s, CH3), 2.58 (6 H, s, 2 × CH3), 6.90
(2 H, s), 7.24 (2 H, d), 7.65 (2 H, d); MS (EI) m/z 274 (Mϩ),
256 (100%), 208, 193, 165, 117, 91, 65.
(4-Methoxyphenyl) o- and p-tolyl sulfone 12.7c Solid; IR (KBr)
1156, 1315 cmϪ1; 1H NMR (200 MHz; CDCl3) δ 2.36 and 2.43
(Me, 2 s, p-12 and o-12), 3.78 and 3.81 (MeO, 2 s, o-12 and
p-12), 6.91 (2 H, d), 7.24 (2 H, d), 7.78–7.87 (4 H, 2 d).
2- and 4-Chlorophenyl methyl sulfone 13.6e Liquid; IR (film)
1154, 1316 cmϪ1; 1H NMR (200 MHz; CDCl3) δ 2.96 and 3.17
(CH3, 2 s, p-13 and o-13), 7.47–8.05 (m, 4 H).
8 (a) F. Effenberger and K. Huthmacher, Chem. Ber., 1976, 109, 2315;
(b) M. Ono, Y. Nakamura, S. Sato and I. Itoh, Chem. Lett., 1988,
395.
9 (a) J. H. Clark and D. Macquarrie, Chem. Soc. Rev., 1996, 25, 303;
(b) M. Balogh and P. Laszlo, Organic Chemistry using Clays,
Springer-Verlag, New York, 1993; (c) A. Finiels, P. Geneste,
J. Lecomte, F. Marichez, C. Moreau and P. Moreau, J. Mol. Catal.
A: Chem., 1999, 148, 165; (d) T. J. Pinnavaia, Science, 1983, 220,
365; (e) R. S. Drago and E. E. Getty, J. Am. Chem. Soc., 1988, 110,
3311; (f) J. M. Thomas, Angew. Chem., Int. Ed. Engl., 1994, 33, 913;
(g) R. A. Sheldon, Chem. Ind. (London), 1997, 12.
(4-Chlorophenyl) phenyl sulfone 14.6h Solid; IR (KBr) 1152,
1
1318 cmϪ1; H NMR (200 MHz; CDCl3) δ 7.50 (5 H, m), 7.85
(4 H, m).
(4-Chlorophenyl) p-tolyl sulfone 15.6h Solid; IR (KBr) 1153,
1
1315 cmϪ1; H NMR (200 MHz; CDCl3) δ 2.39 (3 H, s, CH3),
10 S. E. Sen, S. M. Smith and K. A. Sullivan, Tetrahedron, 1999, 55,
7.27 (2 H, d), 7.45 (2 H, d), 7.77 (2 H, d), 7.84 (2 H, d); MS (EI)
m/z 268 [Mϩ(37Cl), 19%], 266 [Mϩ(35Cl), 51], 161, 159, 139 (100),
107, 91, 65.
12657.
11 (a) B. M. Choudary, M. Sateesh, M. L. Kantam and K. V. R.
Prasad, Appl. Catal. A., 1998, 171, 155; (b) B. M. Choudary, M. L.
Kantam, M. Sateesh, K. K. Rao and P. L. Santhi, Appl. Catal. A.,
1997, 149, 257.
12 (a) A. X. Li, T. S. Li and T. H. Ding, Chem. Commun., 1997, 1389;
(b) D. E. Ponde, V. H. Deshpande, V. J. Bulbule, A. Sudalai and A. S.
Gajare, J. Org. Chem., 1998, 63, 1058.
(4-Bromophenyl) p-tolyl sulfone 16. Solid, mp 134 ЊC (lit.,6h
1
135–136 ЊC); IR (KBr) 1152, 1314 cmϪ1; H NMR (200 MHz;
CDCl3) δ 2.40 (3 H, s, CH3), 7.28 (2 H, d), 7.61 (2 H, d), 7.78
(2-,2Ј-, 6-,6Ј-H, m); MS (EI) m/z 312 [Mϩ(81Br), 21%], 310
[Mϩ(79Br), 23], 205, 203, 139 (100), 107, 91, 79, 77, 76, 65, 75,
50.
13 F. Bigi, L. Chesini, R. Maggi and G. Sartori, J. Org. Chem., 1999, 64,
1033.
14 (a) S. J. Barlow and C. Calvert, Environmentally-Friendlier Catalysts
Using Non-Toxic Supported Reagents, BACS Symposium at
Chemspec Europe, 1993; (b) K. Smith, G. M. Ewart and K. R.
Randles, J. Chem. Soc., Perkin Trans. 1, 1997, 1085; (c) S. Daley,
K. A. Trevor, K. R. Randles and B. D. Gott, PTC Int. Appl. WO93
18. 000, 1993 (Chem. Abstr., 1994, 120, P54320u).
Acknowledgements
N. S. C. thanks the Council of Scientific and Industrial
Research (CSIR), India for the award of a Research Fellowship.
15 B. M. Choudary, N. S. Chowdari, M. L. Kantam and R. Kannan,
Tetrahedron Lett., 1999, 40, 2859.
16 P. Laszlo, A. Mathy, Helv. Chim. Acta, 1987, 70, 577.
17 R. D. Laura, Clay Min., 1976, 11, 331.
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