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G. Signore et al.
SHORT PAPER
13C NMR: d = 21.8, 25.8, 26.0, 31.5, 127.8, 128.9, 130.1, 138.2,
(2) (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2001, 335;
and references therein. (b) Drabowicz, J.; Kielbasinski, P.;
Mikolajczyk, M. In The Chemistry of Sulphones and
Sulphoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.;
John Wiley & Sons: Chichester UK, 1988, 233.
144.3, 151.4.
GC-MS: m/z (%) = 208 (M+·, 19), 177 (17), 160 (41), 145 (100), 110
(31), 77 (24).
(3) (a) Baciocchi, E.; Gerini, M. F.; Lapi, A. J. Org. Chem.
2004, 69, 3586. (b) Russel, G. A.; Ochrymowycz, L. A. J.
Org. Chem. 1960, 35, 2016. (c) Mikolajczyk, M.;
Grzejszczak, S.; Midura, W.; Zatorski, A. Synthesis 1976,
396. (d) Craig, D.; Daniels, K.; Marsh, A.; Rainford, D.;
Smith, A. M. Synlett 1990, 531. (e) Mikolajczyk, M.;
Perlikowska, W. O.; Melanczuk, J.; Crzstau, H. J.;
Perraudarcy, A. Synlett 1991, 913.
(E)-Phenyl 2-Cyclohexylethenyl Sulfoxide13
Yellowish oil.
1H NMR: d = 1.0–1.2 (m, 5 H), 1.5–1.8 (m, 5 H), 2.10 (m, 1 H), 6.10
(dd, J = 15.4, 1.1 Hz, 1 H), 6.51 (dd, J = 15.4, 6.2 Hz, 1 H), 7.4–7.6
(m, 5 H).
13C NMR: d = 25.5, 25.7, 31.55, 31.65, 40.25, 124.4, 129.2, 130.7,
132.8, 144.15, 146.4.
(4) Mikolajczyk, M.; Perlikowska, W.; Omelanczuk, J.; Cristau,
H. J.; Perraud-Darcy, A. J. Org. Chem. 1998, 63, 9716.
(5) (a) Huang, X.; Duan, D.; Zheng, W. J. Org. Chem. 2003, 68,
1958. (b) Zhong, P.; Guo, M.-P.; Huang, X. J. Chem. Res.,
Synop. 2000, 588. (c) Zhong, P.; Huang, X.; Guo, M.-P.
Tetrahedron 2000, 56, 8921. (d) Zhong, P.; Huang, X.; Guo,
M.-P. Synth. Commun. 2001, 31, 615.
(6) (a) Hogg, D. R. In The Chemistry of Sulfenic Acids and their
Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester,
UK, 1990, 361. (b) Van den Breok, L. A. G. M.;
Delbressine, L. P. C.; Ottenheijm, J. C. J. In The Chemistry
of Sulfenic Acids and their Derivatives; Patai, S., Ed.; John
Wiley & Sons: Chichester, UK, 1990, 701. (c) Kosugi, H.;
Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org.
Chem. 1987, 52, 1078. (d) Posner, G. H.; Tang, P. W. J.
Org. Chem. 1978, 43, 4131. (e) Cardellicchio, C.;
Fiandanese, V.; Naso, F. J. Org. Chem. 1992, 57, 1718.
(7) (a) Jahnke, D.; Reinheckel, H. Organomet. Chem. Synth.
1970, 1, 31. (b) Reinheckel, H.; Jahnke, D. Chem. Ber.
1966, 99, 1718. (c) Reinheckel, H.; Haage, K.; Jahnke, D.
Organomet. Chem. Rev., Sect. A 1969, 4, 47. (d) Janke, D.;
Reinheckel, H. Ger Patent 1248656, 1967; Chem. Abstr.
1967, 66, 49731. (e) Reinheckel, H.; Jahnke, D.
GC-MS: m/z (%) = 234 (M+·, 5), 219 (18), 218 (100), 186 (18), 136
(36), 109 (71), 67 (63).
(E)-4¢-Methylphenyl Hex-1-enyl Sulfoxide14
Yellow oil.
1H NMR: d = 0.88 (t, J = 7.0 Hz, 3 H), 1.2–1.5 (m, 4 H), 2.22 (dtd,
J = 7.0, 6.6, 1.5 Hz, 2 H), 2.40 (s, 3 H), 6.20 (dt, J = 15.0, 1.5 Hz, 1
H), 6.59 (dt, J = 15.0, 7.0 Hz, 1 H), 7.3–7.5 (m, 4 H).
13C NMR: d = 14.0, 21.6, 22.3, 30.4, 31.9, 124.8, 130.2, 135.3,
135.3, 141.2, 141.4, 141.5.
GC-MS: m/z (%) = 222 (M+·, 5), 206 (11), 174 (67), 131 (100), 123
(29), 91 (29).
(E)-Methyl Hex-1-enyl Sulfoxide12
Yellow oil.
1H NMR: d = 0.91 (t, J = 7 Hz, 3 H), 1.25–1.55 (m, 4 H), 2.24 (dtd,
J = 7.0, 6.4, 1.5 Hz, 2 H), 2.60 (s, 3 H), 6.27 (dt, J = 15.0, 1.5 Hz, 1
H), 6.49 (dt, J = 15.0, 6.6 Hz, 1 H).
13C NMR: d = 14.0, 22.4, 30.4, 31.9, 41.0, 134.2, 141.2.
GC-MS: m/z (%) = 146 (M+·, 49), 129 (11), 117 (12), 103 (10), 81
(51), 55 (100), 41 (72).
Abhandlungen der Deutschen Akademie der Wissenschaften
zu Berlin Klasse fuer Chemie Geologie und Biologie;
Akademie Verlag: Berlin, 1967, 67. (f) Reinheckel, H.;
Jahnke, D. Gb Patent 1062405, 1967; Chem. Abstr. 1967, 67,
473356. (g) Reinheckel, H.; Jahnke, D. Dd Patent 51311,
1967; Chem. Abstr. 1967, 66, 104821. (h) Reinheckel, H.;
Jahnke, D. Dd Patent 50599, 1966; Chem. Abstr. 1967, 66,
75814.
Acknowledgment
Financial support by the Università di Pisa is acknowledged. The
authors thank Prof. G. Sbrana for use of instruments required and
Mr. M. Martinelli for technical assistance.
(8) Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification
of Laboratory Chemicals; Pergamon: New York, 1983.
(9) Feuvrie, C.; Blanchet, J.; Bonin, M.; Micouin, L. Org. Lett.
2004, 6, 2333.
References
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Synthesis 2006, No. 5, 762–764 © Thieme Stuttgart · New York