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S. S. Kim et al.
SHORT PAPER
Ethyl Phenyl Sulfoxide (Entry 8)14
1H NMR (CDCl3, 200 MHz): = 2.73 (m, 2 H), 2.99 (m, 2 H), 3.83
(m, 2 H), 4.54 (m, 2 H).
13C NMR (CHCl3, 50 MHz): = 46.54, 59.29.
1H NMR (CDCl3, 200 MHz): = 1.20 (t, 3 H, J = 7.6 Hz), 2.82 (dq,
2 H, J = 12.8 Hz), 7.46–7.65 (m, 5 H).
13C NMR (CHCl3, 100 MHz): = 5.80, 50.10, 123.99, 128.98,
130.77, 143.07.
Acknowledgement
MS (EI, 70 eV): m/z = 126, 110, 97, 78, 65, 51, 39.
The authors warmly thank Korea Science and Engineering Founda-
tion for the financial support (R01-2001-00057).
Benzyl Methyl Sulfoxide (Entry 9)22
1H NMR (CDCl3, 200 MHz): = 2.46 (t, 3 H), 3.87 (d, 1 H, J = 12.8
Hz), 4.06 (d, 1 H, J = 12.8 Hz), 7.27–7.40 (m, 5 H).
References
13C NMR (CHCl3, 100 MHz): = 37.25, 60.26, 128.43, 128.97,
129.59, 129.99.
(1) Dr. Kasi Nehru is a visiting scholar from Madurai Kamaraj
University on a grant from BK 21(2001).
Benzyl Ethyl Sulfoxide (Entry 10)
(2) (a) Hollingworth, G. J. In Comprehensive Organic
Functional Group Transformations, Vol. 2; Katritzky, A. R.;
Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds.; Elsevier:
Oxford, 1995. (b) The Synthesis of Sulfones, Sulfoxides and
Cyclic Sulfides; Patai, S.; Rappoport, Z., Eds.; Wiley: New
York, 1994.
(3) Ravikumar, K. S.; Bégué, J.-P.; Bonnet-Delpon, D.
Tetrahedron Lett. 1998, 39, 3141.
(4) Gasparrini, F.; Giovannoli, M.; Misiti, D. J. Org. Chem.
1990, 55, 1323.
1H NMR (CDCl3, 200 MHz): = 1.34 (t, 3 H, J = 7.4 Hz), 2.61 (dq,
2 H, J = 8 Hz), 3.99 (q, 2 H, J = 12.8 Hz), 7.28–7.45 (m, 5 H).
13C NMR (CHCl3, 100 MHz): = 6.53, 43.96, 57.48, 128.25,
128.90, 129.83, 129.88.
MS (EI, 70 eV): m/z = 168, 91, 77, 65, 51, 39.
Diphenyl Sulfoxide (Entry 11)14
Mp 68 °C (Lit.23 mp 69–71 °C).
1H NMR (CDCl3, 200 MHz): = 7.43–7.68 (m).
13C NMR (CHCl3, 50 MHz): = 124.89, 129.38, 131.10, 145.83.
(5) Roh, K. R.; Kim, K. S.; Kim, Y. H. Tetrahedron Lett. 1991,
32, 793.
(6) Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H.
Synthesis 1995, 1357; and references therein.
(7) Arterburn, J. B.; Nelson, S. L. J. Org. Chem. 1996, 61, 2260.
(8) Bonadies, F.; Angelis, F. D.; Locati, L.; Scettri, A.
Tetrahedron Lett. 1996, 37, 7129.
(9) Sevvel, R.; Rajagopal, S.; Srinivasan, C.; Alhaji, N. I.;
Chellamani, A. J. Org. Chem. 2000, 65, 3334.
(10) Pautet, F.; Daudon, M. Tetrahedron Lett. 1991, 32, 1457.
(11) Ali, M. H.; Stevens, W. C. Synthesis 1997, 764; and
references cited therein.
Benzyl Phenyl Sulfoxide (Entry 12)14
Mp 121 °C (Lit.23 mp 122–123 °C).
1H NMR (CDCl3, 200 MHz): = 3.98 (d, 1 H, J = 12.8 Hz), 4.09 (d,
1 H, J = 12.8 Hz), 6.95–7.00 (m, 2 H), 7.22–7.28 (m, 3 H), 7.35–
7.45 (m, 5 H).
13C NMR (CHCl3, 100 MHz): = 63.07, 123.95, 127.78, 127.98,
128.39, 128.65, 129.90, 130.71, 142.25.
Dibenzyl Sulfoxide (Entry 13)14
(12) Ali, M. H.; Bohnert, G. J. Synthesis 1998, 1238.
(13) (a) Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron
Lett. 1995, 36, 3825. (b) Kropp, P. J.; Breton, G. W.; Fields,
J. D.; Tung, J. C.; Loomis, B. R. J. Am. Chem. Soc. 2000,
122, 4280.
(14) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J. H.; Morimotoa, T.
Synthesis 1997, 1161; and references cited therein.
(15) (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis;
Academic Press: San Diego, 1997. (b) Stang, P. J.;
Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
(16) Srinivasan, C.; Chellamani, A.; Kuthalingam, P. J. Org.
Chem. 1982, 47, 428.
Mp 133 °C (Lit.14 mp 133–135 °C).
1H NMR (CDCl3, 200 MHz): = 3.85 (d, 2 H, J = 12.8 Hz), 3.92 (d,
2 H, J = 12.8 Hz), 7.25–7.38 (m, 10 H).
13C NMR (CHCl3, 100 MHz): = 57.12, 128.25, 128.84, 130.06,
130.03.
Dipropyl Sulfoxide (Entry 14)14
1H NMR (CDCl3, 200 MHz): = 1.08 (t, 6 H, J = 7.2 Hz), 1.85
(sext, 4 H, J = 7.6 Hz), 2.50–2.74 (m, 4 H).
13C NMR (CHCl3, 100 MHz): = 13.41, 16.26, 54.36.
(17) Ochiai, M.; Nakanishi, A.; Ito, T. J. Org. Chem. 1997, 62,
4253.
(18) Barton, D. H. R.; Li, W.; Smith, J. A. Tetrahedron Lett.
1998, 39, 7055.
Dibutyl Sulfoxide (Entry 15)11
1H NMR (CDCl3, 200 MHz): = 0.92 (t, 6 H, J = 7.2 Hz), 1.37–1.50
(m, 4 H), 1.70 (quin, 4 H, J = 7.4 Hz), 2.57–2.66 (m, 4 H).
(19) Tohma, H.; Takizawa, S.; Watanabe, H.; Fukuoka, Y.;
Maegawa, T.; Kita, Y. J. Org. Chem. 1999, 64, 3519.
(20) Kim, S. S.; Nehru, K. Synlett 2002, 616.
(21) Murray, R. W.; Jeyaraman, R.; Pillay, M. K. J. Org. Chem.
1987, 52, 746.
13C NMR (CHCl3, 100 MHz): = 13.27, 21.66, 24.22, 51.76.
Chloromethyl Phenyl Sulfoxide (Entry 16)24
1H NMR (CDCl3, 200 MHz): = 4.41 (s, 2 H), 7.56–7.60 (m, 3 H),
7.69–7.74 (m, 2 H).
(22) Pouchert, C. J.; Behnke, J. The Aldrich Library of 13C and 1H
FT NMR Spectra, 1st ed., Vol.2; Aldrich: USA, 1993.
(23) Oae, B. S.; Ohnishi, Y.; Kozuka, S.; Tagaki, W. Bull. Chem.
Soc. Jpn. 1966, 39, 364.
13C NMR (CHCl3, 50 MHz): = 61.43, 124.91, 129.45, 132.27.
1,4-Thioxane-4-oxide (Entry 17)11
Mp 42 °C (Lit.25 mp 41–43 °C).
(24) Hojo, M.; Yoshida, Z. J. Am. Chem. Soc. 1968, 90, 4496.
(25) Liu, K.-T.; Tong, Y.-C. J. Org. Chem. 1978, 43, 2717.
Synthesis 2002, No. 17, 2484–2486 ISSN 0039-7881 © Thieme Stuttgart · New York