Promoted by SmI3, phenacyl thiocyanates can undergo efficiently dethiocyanation and thus give a samarium enolate intermediate. On treatment with water or aldehydes and water subsequently, this in situ generated intermediate can give acetophenones or α,β-unsaturated ketones respectively in high yields under mild conditions.
(a) KriefA., and LavalA. M., Chem. Rev., 1999, 99, 745; (b) G. A. Molander and C. R. Harris, Tetrahedron, 1998, 54, 3321; (c) G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
2.
LucheJ.L., and GemalS. L., J. Am. Chem. Soc., 1979, 101, 5848.
3.
FukuzawaS., FujinamiT., YamauchiS., and SakaiS., J. Chem. Soc., Perkin Trans. 1, 1986, 1929.
4.
ImamotoT., TakiyamaN., and NakamuraK., Tetrahedron Lett., 1985, 26, 4763.
5.
FukuzawaS., TsurutaT., and SakaiS., J. Chem. Soc., Perkin Trans. 1, 1987, 1473.
6.
YuY.P., LinR. H., and ZhangY. M., Tetrahedron Lett., 1993, 34, 4547.
7.
ChenX.Y., BaoW. L., and ZhangY. M., Chin. Chem. Lett., 2000, 11, 483.
8.
BaoW.L., and ZhangY. M., Synth. Commun., 1996, 26, 3025.
9.
HenningL., Acta Chem. Scand., 1960, 14, 1927.
10.
Beilstein, VII, 1923, p. 283.
11.
(a) HoT.L., synth. Commun., 1979, 9, 241; (b) A. L. Gemal and J. L. Luche, Tetrahedron Lett., 1980, 21, 3195.
12.
NancyL.S., and DavidW. B.Jr., J. Org. Chem., 1970, 35, 759.
13.
(a) BrwonC.D., ChongJ. M., and ShenL. X., Tetrahedron, 1999, 55, 14233; (b) B. C. Ranu, S. K. Guchhait and M. Saha, J. Indian Chem. Soc., 1999, 76, 161; (c) B. C. Ranu, A. Hajra and U. Jana, Synlett, 2000, 1, 75; (d) A. R. Katritzky, A. A. Abdel-Fattah, D. O. Tymoshenko and S. A. Essawy, Synthesis, 1999, 12, 2114.
14.
BowdenK., PozzoA. D., and DuahC. K., J. Chem. Res.(M), 1990, 2801.
15.
(a) BraudeE.A., ForbesW. F., and GoftonB. F.J. Chem. Soc., 1957, 4711; (b) P. G. Farrell and B. A. Read, Can. J. Chem., 1968, 46, 3685; (c) A. Fuentes, J. M. Marinas and J. V. Sinisterra, Tetrahedron Lett., 1987, 28, 4541.