Reactions of azoalkenes derived from hydrazones of ethyl bromopyruvate with ele...

• Author(s): Clarke, S ; Gilchrist, Thomas L. ; Lemos, A. ; G. Roberts, Tony
• Date: 1991
• Persistent ID: http://hdl.handle.net/10400.1/934
• Origin: Sapientia - Universidade do Algarve
• Subject(s): Cicloadição; Diels-Alder; Heterocycles
• Document Type: Article
• Language: English

Description

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.