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LETTER
3781. (d) Yoo, B. W.; Choi, K. H.; Lee, S. J.; Yoon, C. M.;
Kim, S. H.; Kim, J. H. Synth. Commun. 2002, 32, 63.
(e) Somasundaran, N.; Srinivasan, C. Ind. J. Chem., Sect. B
2002, 41, 1523. (f) Yoo, B.; Choi, K. H.; Kim, D. Y.; Choi
Kyung, II.; Kim, J. H. Synth. Commun. 2003, 33, 53.
reaction, the reaction mixture was diluted with EtOAc and
filtered. The residue was washed with EtOAc several times,
and the combined filtrate and washings were dried (Na2SO4)
and evaporated to dryness. Finally, the crude product thus
obtained was purified by column chromatography using
EtOAc and hexane as eluent and characterized by IR, NMR
and elemental analysis.19
(6) (a) Drabowicz, J.; Togo, H.; Mikolajczyk, M.; Oae, S. Org.
Prep. Proced. Int. 1984, 16, 171. (b) Nuzzo, R. G.; Simon,
H. J.; Filippo, J. S. Jr. J. Org. Chem. 1977, 42, 568.
(c) Chasar, D. W. J. Org. Chem. 1971, 36, 613.
(7) Amos, R. A. J. Org. Chem. 1985, 50, 1311; and references
cited therein.
(8) (a) Lee, G. H.; Choi, E. B.; Lee, E.; Pak, C. S. Tetrahedron
Lett. 1994, 35, 2195. (b) Hepworth, H.; Clapham, H. N. J.
Chem. Soc. 1921, 119, 1188.
(9) (a) Gazder, M.; Smiles, S. J. Chem. Soc. 1910, 97, 2248.
(b) Kobayashi, K.; Kubota, Y.; Furukawa, N. Chem. Lett.
2000, 400.
(10) (a) Dyer, J. C.; Evans, S. A. Jr. J. Org. Chem. 1980, 45,
5350. (b) Dilajan, H. S.; Weber, W. P. Tetrahedron Lett.
1970, 969.
(19) Ethyl Octadecyl Sulfide: 1H NMR (300 MHz): d = 0.88 (t,
J = 6.0 Hz, 3 H, -CH3), 1.35 (m, 33 H, CH2-, -CH3), 1.55 (m,
2 H, -CH2-), 2.53 (m, 4 H, -CH2SCH2-). IR: 2925, 2863,
1465, 723 cm–1. Anal. Calcd for C20H42S: C, 76.35; H, 13.46;
S, 10.19. Found: C, 76.52; H, 13.17; S, 10.38.
n-Pentyl-2-hydroxyethyl Sulfide: 1H NMR (300 MHz): d =
0.88 (t, J = 6.0 Hz, 3 H, -CH3), 1.34 (m, 4 H, 2-CH2-), 1.57
(m, 2 H, -CH2-), 2.50 (t, J = 7.2 Hz, 2 H, -SCH2-), 2.70 (t,
J = 6.0 Hz, 2 H, -SCH2-), 3.69 (t, J = 6.0 Hz, 2 H, -CH2-O-).
IR: 3391, 2960, 2935, 2858, 1465, 1050, 1015, 774 cm–1.
Anal. Calcd for C9H18O2S: C, 56.80; H, 9.53; S, 16.85.
Found: C, 57.12; H, 9.36; S, 17.14.
n-Pentyl Phenyl Sulfide: 1H NMR (300 MHz): d = 0.87 (t,
J = 7.0 Hz, 3 H, -CH3), 1.37 (m, 4 H, 2-CH2-), 1.65 (m, 2 H,
-CH2-), 2.8 (t, J = 7.11 Hz, 2 H, -S-CH2-), 7.54 (m, 5 H,
aromatic). IR: 2930, 2858, 1588, 1486, 1107, 1025, 748
cm–1. Anal. Calcd for C11H16S: C, 73.27; H, 8.94; S, 17.78.
Found: C, 73.43; H, 9.18; S, 17.52.
(11) Johnson, C. R.; Bacon, C. C.; Rigau, J. J. J. Org. Chem.
1972, 37, 919.
(12) Oae, S.; Kawamura, S. Bull. Chem. Soc. Jpn. 1963, 36, 163.
(13) Nagata, T.; Yoshimura, T.; Fujimori, K.; Oae, S.
Tetrahedron Lett. 1984, 25, 341.
(14) (a) Saikia, A. K.; Tsuboi, S. J. Org. Chem. 2001, 66, 643.
(b) Kar, G.; Saikia, A. K.; Bora, U.; Dehury, S. K.;
Chaudhuri, M. K. Tetrahedron Lett. 2003, 44, 4503.
(15) (a) Sarmah, B. K.; Barua, N. C. Tetrahedron 1991, 47,
8587. (b) Bezbarua, M. S.; Bez, G.; Barua, N. C. Chem. Lett.
1999, 325.
2-Ethylsulfinyl Ethyl Acetate: 1H NMR (300 MHz): d =
1.38 (t, J = 7.38 Hz, 3 H, -CH3), 2.07 (s, 3 H, CH3CO-), 2.55
(t, J = 7.50 Hz, 2 H, -CH2S-), 2.74 (t, J = 7.50 Hz, 2 H,
-CH2S-), 4.22 (t, J = 6.90 Hz, 2 H, -CH2-OAc). IR: 2965,
2924, 1741, 1460, 1229, 1034, 748 cm–1.
Phenysulfinylacetone: 1H NMR (400 MHz): d = 2.27 (s, 3
H, -CH3), 3.66 (s, 2 H, -SOCH2CO-), 7.21 (m, 2 H, ArH),
7.32 (m, 3 H, ArH). 13C NMR (100 MHz): d = 28.42, 45.06,
127.10, 129.35, 129.70, 134.84, 203.56. IR: 3073, 2935,
1711, 1358, 1235, 1163, 1025, 743 cm–1.
(16) Wang, W. B.; Shi, L. L.; Huang, Y. Z. Tetrahedron Lett.
1990, 31, 1185.
(17) Barua, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S.
Tetrahedron Lett. 1996, 37, 4559.
(18) General Procedure:
(20) (a) Shiota and co-workers prepared precipitated nickel by
adding wet NiCl2·6H2O and hot zinc powder. See: Ishige,
M.; Shiota, M. Can. J. Chem. 1975, 53, 1700. (b) When
added to NiCl2·6H2O, aluminum powder reacts vigorously
without heating. The reaction must be cooled for the heat to
subside.
In a typical procedure, NiCl2·6H2O (10 mmol) and
aluminum powder (10 mmol) were added to an ice-cooled
solution of the substrate (1.0 mmol) in freshly distilled THF.
An exothermic reaction took place immediately and stirring
was continued for a specified period of time. The reaction
mixture was monitored by TLC. After completion of the
Synlett 2005, No. 2, 358–360 © Thieme Stuttgart · New York