Commercially available anhydrous KF without activation or solid support promotes condensation between active methylene compounds, carbon disulfide and an alkylating agent in dry DMF to allow the preparation of a variety of ketene dithioacetals in fair to good yields under ambient conditions.
References
1.
DieterR. K., Tetrahedron, 1986, 42, 3029; H. Junjappa, H. Ila and C. V. Asokan, Tetrahedron, 1990, 46, 5423; M. Kolb, Synthesis, 1990, 171; W.-D. Rudorf, Sulfur Rep., 1991, 11, 51; Y. Tominaga, S. Kohra, H. Honkawa and A. Hosomi, Heterocycles, 1989, 29, 1409; K. M. Yadav, J. R. Suresh, B. Patro, H. Ila and H. Junjappa, Tetrahedron, 1996, 52, 4679.
2.
KelberC., Chem. Ber., 1910, 43, 1252; A. Thuillier and J. J. Vialle, Bull. Soc. Chim. Fr., 1959, 1398; A. Thuillier and J. J. Vialle, Bull. Soc. Chim. Fr., 1962, 2194; I. Shahak and Y. Sasson, Tetrahedron Lett., 1973, 14, 4207; R. K. Dieter, Tetrahedron, 1981, 46, 5031; H. Junjappa and S. M. S. Chauhan, Tetrahedron, 1976, 32, 1779.
3.
DalgaardL., JensenL., and LawessonS. O., Tetrahedron, 1974, 30, 93.
4.
ClarkJ., Chem. Rev., 1980, 80, 429.
5.
YawamakiJ., and AndoT., Chem. Lett., 1979, 755; P. Laszlo and P. Pennetreau, Tetrahedron Lett., 1985, 26, 2645; D. E. Bergbreiter and J. L. Lalonde, J. Org. Chem., 1987, 52, 1601; A. K. S. B. Rao, C. G. Rao and B. B. Singh, Synth. Commun., 1991, 21, 443; W. J. Smith and J. S. Sawyer, Tetrahedron Lett., 1996, 37, 299.
6.
VilleminD., and AbdelkrimA., Synthesis, 1991, 301.
7.
AugustinM., and GrothC., J. Prakt. Chem., 1979, 321, 205.
8.
KhanA. Z., and SandstromJ., J. Chem. Soc., Perkin Trans. 1, 1988, 2085.
9.
ChadwickD. J., ChambersJ., MacraeR., MeakinsG. D., and SnowdoenR. L., J. Chem. Soc., Perkin Trans. 2, 1976, 597; M. X. Wang, J. M. Liang and Z. T. Huang, J. Chem. Res. (S), 1994, 166.
10.
YatesP., LynchT. R., and MooreD. R., Can. J. Chem., 1971, 49, 1467.
