Journal of Organic Chemistry p. 1842 - 1848 (1992)
Update date:2022-09-26
Topics:
Leardini, Rino
Nanni, Daniele
Tundo, Antonio
Zanardi, Giuseppe
Ruggieri, Fabrizio
Aromatic imines react with phenylacetylene or styrene in an acetonitrile solution of iron(III) chloride to give quinolines 3 or their tetrahydro derivatives 11 together with variable amounts of products 4 arising from the reduction of the imines.The initial step appears to be a one-electron oxidation to generate iron(II) and an imine radical cation.When the reactions are carried out in the presence of stoichiometric amounts of tetrachloro-p-benzoquinone (chloranil), only quinolines 3 are obtained.
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