246
R. P. Singh et al. / Tetrahedron 57 (2001) 241±247
1
ether); H NMR (CDCl3, 400 MHz) d 2.30 (s, 3H) 2.66 (s,
6H), 3.03 (s, 3H), 6.96 (s, 2H).
Acknowledgements
V. K. S. thanks DST (Government of India) for the
Swarnajayanti Fellowship Award (1998). R. M. K. thanks
UGC and K. L. C., P. S., thank CSIR for research fellowships.
1.4.17. Napthylphenylsulfone (20a).34 Solid; mp 69±718C;
Rf 0.45 (10:90 EtOAc/petroleum ether); H NMR (CDCl3,
1
400 MHz) d 7.39±7.57 (m, 6H), 7.79±8.03 (m, 4H), 8.50 (d,
J8.5 Hz, 1H), 8.63 (d, J7.9 Hz, 1H).
References
1.4.18. Napthyltolylsulfone (20b).35 Solid; mp 102±1048C;
1
Rf 0.35 (10:90 EtOAc/petroleum ether); H NMR (CDCl3,
1. (a) Olah, G. A. Friedel±Crafts and Related Reactions; Wiley-
Interscience: New York, 1964; Vol. III. (b). Olah, G. A. Frie-
del±Crafts Chemistry; Wiley-Interscience: New York, 1973.
(c) Heaney, H. Comprehensive Organic Synthesis; Trost,
B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 733±752.
(d). Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Compre-
hensive Organic Synthesis; Trost, B. M., Ed.; Pergamon:
Oxford, 1991; Vol. 3, pp 293±339.
400 MHz) d 2.24 (s, 2.19H, ±Me, b-20b), 2.28 (s, 0.81H, a-
20b), 7.21 (m, 2H), 7.45±7.59 (m, 2H), 7.76±8.06 (m, 5H),
8.49 (d, J8.9 Hz, 1H), 8.67 (d, J8.5 Hz, 1H).
1.4.19. Anisylphenylsulfone (21a). White solid; mp 79±
808C; IR (KBr) 3010, 1280, 720 cm21; Rf 0.28 (10:90
EtOAc/petroleum ether); H NMR (CDCl3, 400 MHz) d
1
2. For some recent papers on catalytic Friedel±Crafts acylation
reaction, see: (a) Kobayashi, S.; Iwamoto, S. Tetrahedron Lett.
1998, 39, 4697. (b). Desmurs, J. R.; Labrouillere, M.; Le
Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J. Tetrahedron
Lett. 1997, 38, 8871. (c). Hachiya, I.; Moriwaki, M.; Kobaya-
shi, S. Tetrahedron Lett. 1995, 36, 409. (d). Kawada, A.;
Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183. (e)
Matsuo, J.-I.; Odashima, K.; Kobayashi, S. Synlett 2000, 403.
3. (a) Kotsuki, H.; Oshisi, T.; Inoue, M. Synlett 1998, 255. (b).
Kotsuki, H.; Oshisi, T.; Inoue, M.; Kojima, T. Synthesis 1999,
603.
3.74 (s, 1.14H, ±OMe, o-21a), 3.82 (s, 1.86H, ±OMe, p-
21a), 6.92 (m, 2H), 7.51 (m, 4H), 7.90 (m, 3H).
1.4.20. Anisyltolylsulfone (21b).35 White solid; mp 80±
828C; Rf 0.35 (10:90 EtOAc/petroleum ether); H NMR
1
(CDCl3, 400 MHz) d 2.33 (s, 2.49H, p-21b), 2.35 (s,
0.51H, o-21b), 3.78 (s, 3H, ±OMe), 6.90 (d, J7.9 Hz,
2H), 7.23 (d, J8.3 Hz, 2H), 7.73 (d, J8.5 Hz, 2H), 7.81
(d, J 8.0 Hz, 2H).
4. Ono, M.; Nakamura, Y.; Sato, S.; Itoh, I. Chem. Lett. 1988,
395.
1.4.21. Dianisylsulfone (21c). Solid, mp 104±1068C; IR
(KBr) 3000, 1250, 710 cm21; Rf 0.20 (10:90 EtOAc/petro-
leum ether); H NMR (CDCl3, 400 MHz) d 3.80 (s, 6H),
6.91 (d, J8.9 Hz, 4H), 7.81 (d, J8.3 Hz, 4H).
5. Effenberger, F.; Huthmacher, K. Chem. Ber. 1976, 109, 2315.
6. Smith, K.; Ewart, G. M.; Randles, K. R. J. Chem. Soc., Perkin
Trans. 1 1997, 1085.
1
7. Choudhary, B. M.; Chowdari, N. S.; Kantam, M. L.; Kannan,
R. Tetrahedron Lett. 1999, 40, 2862.
1.4.22. (Bromophenyl)phenylsulfone (22b).36 White solid;
mp 92±948C; Rf 0.50 (10:90 EtOAc/petroleum ether); H
NMR (CDCl3, 400 MHz) d 7.42±7.86 (m, 9H).
1
8. Repichet, S.; Le Roux, C.; Hernandez, P.; Dubac, J. J. Org.
Chem. 1994, 64, 6479.
9. Repichet, S.; Le Roux, C.; Dubac, J. Tetrahedron Lett. 1999,
40, 9233.
1.4.23. (Bromophenyl)tolylsulfone (22b).37 White solid;
mp 132±1348C; Rf 0.35 (10:90 EtOAc/petroleum ether);
1H NMR (CDCl3, 400 MHz) d 2.40 (s, 3H), 7.30 (d,
J8.3 Hz, 2H), 7.62 (d, J8.3 Hz, 2H), 7.80 (m, 4H).
10. Saravanan, P.; Anand, R. V.; Singh, V. K. Tetrahedron Lett.
1998, 39, 3823.
11. Anand, R. V.; Saravanan, P.; Singh, V. K. Synlett 1999, 415.
12. Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1999, 40, 2611.
13. Chandra, K. L.; Saravanan, P.; Singh, V. K. Synlett 2000, 359.
14. Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 287.
15. Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
16. Baranger, P. M. Bull. Soc. Chim. 1931, 49, 1213.
17. Cohen, W. D. Recl. Trav. Chim. 1919, 38, 113.
18. Ploeg, W. Recl. Trav. Chim. 1926, 45, 342.
19. Lea, T. R.; Robinson, R. J. Chem. Soc. 1926, 2351.
20. Burton, H.; Hu, P. F. J. Chem. Soc. 1948, 601.
21. Buu-Hoi, N. P.; Hoan, N. J. Org. Chem. 1952, 17, 350.
22. Bourget Bull. Soc. Chim. 1896, 15, 945.
1.4.24. (Bromophenyl)-4-methoxyphenylsulfone (22c).
White solid; mp 95±968C; IR (KBr) 2990, 1280,
730 cm21; Rf 0.28 (10:90 EtOAc/petroleum ether); 1H
NMR (CDCl3, 400 MHz) d 3.83 and 3.84 (2s, 3H, o-, p-
22c), 6.93±6.98 (m, 2H), 7.62 (d, J7.8 Hz, 2H), 7.79 (d,
J7.9 Hz, 2H), 7.86 (m, 2H).
1.4.25. (Chlorophenyl)phenylsulfone (23a).38 White solid;
mp 77±788C; Rf 0.50 (10:90 EtOAc/petroleum ether); H
1
23. Wood, A. E.; Travis, E. G. J. Am. Chem. Soc. 1928, 50, 1226.
24. Adair, M. Ber. 1878, 11, 116.
NMR (CDCl3, 400 MHz) d 7.46±7.60 (m, 5H), 7.86±7.96
(m, 4H).
25. Velluz, L.; Joly, R.; Bucourt, R. Compt. Rend. 1959, 248, 114.
26. Burton, H.; Hu, P. F. J. Chem. Soc. 1948, 601.
27. Drews, H.; Seymour, M.; Fields, E. K. J. Am. Chem. Soc.
1961, 3871.
1.4.26. (Chlorophenyl)tolylsulfone (23b).25 White solid;
mp 115±1178C; Rf 0.40 (10:90 EtOAc/petroleum ether);
1H NMR (CDCl3, 400 MHz) d 2.40 (s, 3H), 7.30 (d,
J8.2 Hz, 2H), 7.46 (d, J7.9 Hz, 2H), 7.80 (d,
J7.9 Hz, 2H), 7.86 (d, J8.0 Hz, 2H).
28. Kraft, M. Y.; Uretskaya, G. Y. Zh. Org. Khim. 1965, 1, 696.
29. Shamis, E. M.; Dashevskii, M. M. Zh. Org. Khim. 1966, 2,
280.