• Medientyp: E-Artikel
  • Titel: Synthese und HOFMANN‐Abbau des 1‐(Diphenyl‐hydroxymethyl)‐2,2‐dimethyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisochinolinium‐Ions
  • Beteiligte: Wiegrebe, Wolfgang; Rohrbach‐Munz, Barbara; Awe, Walter; Kirk, Olaf
  • Erschienen: Wiley, 1975
  • Erschienen in: Helvetica Chimica Acta
  • Sprache: Englisch
  • DOI: 10.1002/hlca.19750580639
  • ISSN: 0018-019X; 1522-2675
  • Schlagwörter: Inorganic Chemistry ; Organic Chemistry ; Physical and Theoretical Chemistry ; Drug Discovery ; Biochemistry ; Catalysis
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>The synthesis of the N‐quaternary aminoalcohol <jats:bold>6</jats:bold> is described. Analogous to the aminoalcohols <jats:bold>1</jats:bold> and <jats:bold>2</jats:bold>, <jats:bold>6</jats:bold> on treatment with alkali undergoes fission of the substituent at C(1) as a carbonyl compound, with formation of a N, N‐dimethyl‐1,2,3,4‐tetrahydroisoquinolinium ion, which is further degraded to the corresponding <jats:italic>o</jats:italic>‐vinyl‐benzylamine (<jats:italic>Scheme1</jats:italic>). – As a by‐product of a <jats:italic>Bischler‐Napieralski</jats:italic> ring closure, we observed chlorination of an aromatic ring (yielding <jats:bold>19</jats:bold>).</jats:p>