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Synthesis 1993; 1993(1): 57-59
DOI: 10.1055/s-1993-25792
short paper
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A New Access to 1-Naphthylamines by an Equivalent Semmler-Wolff Reaction

Yves L. Janin* , Emile Bisagni
  • *URA 1387 CNRS Institut Curie, Section de Biologie, Bat. 110 Centre Universitaire, F-91405 Orsay, France
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Publication Date:
17 September 2002 (online)

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A new access to 1-naphthylamines from the corresponding 3,4-di-hydro-1(2H)-naphthalenones (α-tetralones) is described. It proceeds in a two-step sequence: preparation of the benzyl Schiff's base of an α-tetralone followed by aromatization over palladium catalyst, which happened to hydrogenolyze the benzyl group at the same time. Five 1-naphthylamines were prepared using this alternative path to the Semmler-Wolff reaction.