Trichloroacetylhydrazones: new highly reactive alkylating agents

Abstract

The behavior of trichloroacylhydrazones as new highly reactive alkylating agents is disclosed; various secondary amines are alkylated within a few minutes at room temperature, and similar alkylating reductions were found with malonates.

References

1. R. O. Hutchins and M. K. Hutchins, Comprehensive Organic Synthesis, ed. I. Fleming and B. M. Trost, Pergamon, Oxford, 1991, vol. 8, pp. 327–362 and references cited therein.
2. R. M. Adlington and A. G. M. Barrett, Acc. Chem. Res., 1983, 16, 55.
3. A. Eschenmoser, D. Felix and G. Ohloff, Helv. Chim. Acta, 1967, 50, 708.
4. L. El Kaim, I. Le Menestrel and R. Morgentin, Tetrahedron Lett., 1998, 39, 6885.
5. R. M. Kellogg, Comprehensive Organic Synthesis, ed. I. Fleming and B. M. Trost, Pergamon, Oxford, 1991, vol. 8, pp. 84–86 and references cited therein.
6. C. N. Yiannios, A. C. Hazy and J. V. Karabinos, J. Org. Chem., 1968, 33, 2076.
7. O. A. Attanasi and P. Filippone, Synlett, 1997, 1128.
8. Alternative intermediates such as oxadiazoles and diazo compounds can be easily proposed in the alkylation process; several analogues of these compounds have been isolated during a study on the basic treatment of the related monochloroacylhydrazones: E. C. Taylor, N. F. Haley and R. J. Clemens, J. Am. Chem. Soc., 1981, 103, 7743 The experiments conducted in EtOH are however difficult to explain with these intermediates.