6808
A. Alizadeh et al. / Tetrahedron Letters 48 (2007) 6805–6808
3. (a) Willams, T. M.; Ciccarone, T. M.; MacTough, S. C.;
14. General procedure for sulfonylation: To a solution of
aromatic compound (1 mmol) and sulfonic acid (1 mmol)
in nitromethane (2 ml), Tf2O (0.25 ml, 1.5 mmol) was
added. The reaction was stirred magnetically at room
temperature and monitored by TLC. On completion of the
reaction, the solvent was evaporated and then aqueous
saturated NaHCO3 (20 ml) was added to destroy the
unreacted sulfonic acid and Tf2O. The resulting precipi-
tated crude product was purified by recrystallization from
a mixture of dichloromethane and n-hexane (1:2) or water
and ethanol. Selected spectroscopic data: (2,4,6-Trimeth-
ylphenyl)tolylsulfone. White solid; mp 114–116 °C (lit.17
117 °C); IR (KBr): 1142, 1299 cmÀ1 (SO2); 1H NMR
(CDCl3, 200 MHz): d 2.33 (s, 3H), 2.44 (s, 3H), 2.63 (s,
6H), 6.98 (s, 2H), 7.3 (d, J = 7.9 Hz, 2H), 7.71 (d,
J = 8.1 Hz, 2H); 13C NMR (CDCl3, 50 MHz): d 20.9,
21.4, 22.7, 125.9, 126.2, 129.4, 132.1, 139.8, 140.6, 143.1,
143.3. (2,4,6-Trimethylphenyl)phenylsulfone. White soliÀd1;
mp 78–80 °C (lit.18 78–79 °C); IR (KBr): 1152, 1305 cm
(SO2); 1H NMR (CDCl3, 200 MHz): d 2.34 (s, 3H), 2.63 (s,
6H), 6.98 (s, 2H), 7.47–7.58 (m, 3H), 7.83 (d, J = 7.7 Hz,
2H); 13C NMR (CDCl3, 50 MHz): d 20.9, 21.3, 125.8,
126.1, 128.8, 132.1, 132.5, 133.7, 140.0, 143.3. (2,4,6-
Trimethylphenyl)methylsulfone. White solid; mp 122–
124 °C (lit.19 122–124 °C); IR(KBr): 1136, 1292 cmÀ1
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1
(SO2); H NMR (CDCl3, 200 MHz): d 2.28 (s, 3H), 2.64
(s, 6H), 3.01 (s, 3H), 6.95 (s, 2H); 13C NMR (CDCl3,
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