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Synthese und Hofmann-Abbau des 1-(Diphenyl-hydroxymethyl)-2,2-dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolinium-Ions

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Wiegrebe, Wolfgang ; Rohrbach-Munz, B. ; Awe, W. ; Kirk, O.
Date of publication of this fulltext: 22 Jun 2010 06:21


Summary. The synthesis of the N-quaternary aminoalcohol 6 is described. Analogous to the
aminoalcohols 1 and 2, 6 on treatment w i t h alkali undergoes fission of the substituent at C(l) as a
carbonyl compound, with formation of a N, N-dimethyl-l,2,3,4-tetrahydroisoquinolinium ion,
which is further degraded to the corresponding o-vinyl-benzylamine {Scheme 7). - As a by-product
of a Bischler-Napieralski ring closure, we observed chlorination of an aromatic ring (yielding 19).

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