reaction mixture was stirred vigorously for a specified time (see
Tables 1–4) at room temperature. The product was extracted with
several portions of diethyl ether and the combined organic extracts
were evaporated in vacuo. The residue was purified by column
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1
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1
H NMR spectra. The spectroscopic characteristics of known
1
987, 53, 1091.
52
53
53
54
55
products 3a, 3b, 3e, 3f and 3g were in agreement with
20 T. Mukaiyana, A. Ikegawa and K. Suzuki, Chem. Lett., 1981, 165.
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2
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1 K. Suzuki, A. Ikegawa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1982,
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2 S. Kobayashi, C. Ogawa, M. Kawamura, M. and M. Sugiura, Synlett,
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,3-Diphenyl-3-(4-fluorophenylsulfanyl)propan-1-one (3c).
◦
1
1981, 983.
White solid, mp 83–85 C. H NMR (300 MHz, CDCl
3
) d 7.89
3 J. Skar z˙ ewski, M. Zieli ´ı ska-Błajet and I. Turowska-Tyrk, Tetrahedron:
Asymmetry, 2001, 12, 1923.
(
2H, d, J = 8.4 Hz, ArH), 7.49–7.61 (2H, m, ArH), 7.45 (2H,
t, J = 6.6 Hz, ArH), 7.12–7.28 (6H, m, ArH), 6.90 (2H, t, J =
24 B. J. Li, L. Jiang, M. Liu, Y. Ch. Chen, L. S. Ding and Y. Wu, Synlett,
2
005, 603.
8
.7 Hz, ArH), 4.36 (1H, t, J = 7.2 Hz, SCH), 3.66 (1H, dd, J =
.1 Hz, 17.1 Hz, CHH), 3.56 (1H, dd, J = 6.0 Hz, 17.1 Hz, CHH);
2
5 M. Marigo, T. Schulte, J. Franzen and K. A. J o¨ rgensen, J. Am. Chem.
Soc., 2005, 127, 1570.
8
1
3
C NMR (75 MHz, CDCl
3
) d 197.0, 162.9 (d, J = 246.6 Hz),
26 J. Franzen, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard
and K. A. J
o¨ rgensen, J. Am. Chem. Soc., 2005, 127, 18296.
1
1
3
41.3, 136.9, 136.2 (d, J = 8.3 Hz), 133.5, 129.2, 128.9, 128.7,
2
2
7 J. D. Holbrey and K. R. Seddon, Clean Prod. Proc., 1999, 1, 223.
28.3, 128.0, 127.6, 116.1 (d, J = 21.5 Hz), 49.3, 44.5; ESMS
8 H. Olivier-Bourbigou and L. Magna, J. Mol. Catal. A: Chem., 2002,
+
59.2 [M + Na] .
1
82–183, 419.
9 J. Dupont, R. F. de Souza and P. A. Z. Suarez, Chem. Rev., 2002, 102,
667.
2
1
,3-Diphenyl-3-(4-tert-butylphenylsulfanyl)propan-1-one (3d).
3
◦
1
White solid, mp 99–101 C. H NMR (300 MHz, CDCl
2H, d, J = 8.1 Hz, ArH), 7.19–7.58 (12H, m, ArH), 4.91 (1H,
dd, J = 6 Hz, 8.1 Hz), 3.64 (1H, dd, J = 7.5 Hz, 15.2 Hz, CHH),
3
) d 7.86
30 D. Zhao, M. Wu, Y. Kou and E. Min, Catal. Today, 2002, 74, 157.
3
1 Ionic Liquids in Synthesis, ed. P. Wasserscheid and T. Welton, Wiley-
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(
3
3
2 J. S. Wilkes, J. Mol. Catal. A. Chem., 2004, 214, 11.
3 T. Welton, Coord. Chem. Rev., 2004, 248, 2459.
3
.56 (1H, dd, J = 6.9 Hz, 15.2 Hz, CHH), 1.27 (9H, s, 3 × CH
C NMR (75 MHz, CDCl ) d 197.4, 151.1, 141.5, 136.9, 133.4,
32.9, 130.9, 128.8, 128.7, 128.3, 128.0, 127.5, 126.1, 48.6, 45.0,
4.7, 31.4. Elemental analysis: calcd. for C25 26OS: C 80.18%, H
.00%, S 8.55%; found: C 80.27%, H 7.01%, S 8.53%.
3
);
1
3
34 T. P. Loh, L. C. Feng, H. Y. Yang and J. Y. Yang, Tetrahedron Lett.,
3
2
002, 43, 8741.
1
3
7
3
5 P. Kotrusz, I. Kmentov a´ , B. Gotov, S. Toma and E. Sol cˇ aniov a´ , Chem.
Commun., 2002, 2510.
H
36 N. S. Chowdari, D. B. Ramachari and C. F. Barbas, III, Synlett, 2003,
906.
1
3
3
3
4
7 P. Kotrusz, S. Toma, H. G. Schmalz and A. Adler, Eur. J. Org. Chem.,
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8 M. S. Rasalkar, M. K. Potdar, S. S. Mohile and M. M. Salunkhe, J. Mol.
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We are grateful to Dr E. Sol cˇ aniov a´ and her staff for NMR
measurements. This work was supported by the Slovak Grant
Agency VEGA, grant No. 1/0072/03. Authors are grateful to
the referees for their valuable comments and for improving the
language of the paper.
41 B. C. Ranu and S. S. Dey, Tetrahedron, 2004, 60, 4183.
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