Trichloroacetylhydrazones: New highly reactive alkylating agents

Chemical Communications

Volumn , Issue 18, 1999, Pages 1893-1894

  Atlan, V ^a   Kaim, L El ^a   Lacroix, S ^a   Morgentin, R ^a  

^a ENSTA PARISTECH   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; CHLORINE DERIVATIVE; HYDRAZONE DERIVATIVE; MALONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; TEMPERATURE;

EID: 0033592375     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905946f     Document Type: Article

References (8)

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.