Isolation and structure elucidation of the by‐product formed in the aminomethylation of α‐methylstyrene

Pál Sohár, János Lázár, Gábor Bernáth

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Abstract

Aminomethylation of α‐methylstyrene (1) leads to 1,2,3,6‐tetrahydro‐4‐phenylpyridine (3) as main product, together with a significant amount of a previously unknown by‐product. The N‐methyl, O‐acetyl‐N‐methyl, N, O‐diacetyl, N‐(4‐nitrobenzoyl), and (via N → O acyl‐migration) O‐(4‐nitrobenzoyl) derivatives of the by‐product were synthesized. By aromatization of the heteroring, 4‐phenyl‐3‐pyridinemethanol (8a) was obtained. According to these derivatives and their IR, 1H and 13C NMR spectra, the by‐product is 1,2,3,6‐tetrahydro‐4‐phenyl‐3‐pyridinemethanol (4a).

Original languageEnglish
Pages (from-to)551-559
Number of pages9
JournalChemische Berichte
Volume118
Issue number2
DOIs
Publication statusPublished - Jan 1 1985

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ASJC Scopus subject areas

  • Chemistry(all)

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