Tetrahedron p. 395 - 406 (1990)
Update date:2022-08-05
Topics:
Schantl, Joachim G.
Hebeisen, Paul
Aliphatic aldehyde phenylhydrazones 1 were converted into 1-phenylazo-1-alkenes 3 either by the reaction with I2 and pyridine followed by base induced 1,4-elimination of pyridine.HI (Method A), or via N-(4-methylbenzenesulfonyl)-N-phenylhydrazones 7 which undergo 1,4-elimination of p-toluenesulfinic acid upon treatment with KOt-Bu (Method B).Both procedures yield mixtures of configurational isomers of the phenylazo-alkenes EE- and EZ- 3b-3e; Method B is giving rise to the kinetically controlled isomer mixture (EZ-3 predominant), which equilibrates to the thremodynamicratio (EE-3 predominant) as afforded by Method A.
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