Reactions of azoalkenes derived from hydrazones of ethyl bromopyruvate with electron rich alkenes and heterocycles

Clarke, S; Gilchrist, Thomas L.; Lemos, A.; Roberts, Tony G.

http://hdl.handle.net/10400.1/934

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Abstract(s)

Three hydrazones of ethyl bromopyruvate, the dinitrophenylhydrazone 2a, the toluene-4-sulphonylhydrazone 2b and the t-butoxycarbonylhydrazone 2c, have been reacted with a series of nucleophilic alkenes and heterocycles in the presence of sodium carbonate. Azoalkenes 3 are presumed as intermediates and adducts have been isolated. The azoalkenes derived from hydrazones 2a and 2c are found to be useful electrophiles and electrophilic dienes.

Keywords

Cicloadição Diels-Alder Heterocycles

URI

http://hdl.handle.net/10400.1/934

Citation

Clarke, S. Reactions of azoalkenes derived from hydrazones of ethyl bromopyruvate with electron rich alkenes and heterocycles, Tetrahedron, 47, 29, 5615-5624, 1991.