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Unusual products from the synthesis of 3‐(2‐phenylethyl)pyridines by the hydrosulfite reduction of nitrosamines
Author(s) -
Walter Lewis A.,
Chang Wei K.,
Mcglotten James,
Foester Robert
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140109
Subject(s) - chemistry , pyridine , nitroso , medicinal chemistry , mass spectrum , aryl , proton nmr , stereochemistry , organic chemistry , ion , alkyl
The Overberger hydrosulfite reduction of N ‐nitroso[(3‐phenylmethylamino)methyl]pyridine gave 3‐(2‐phenylethyl)pyridine and, as determined by nmr, glc and mass spectral studies, about 15% of a mixture which consisted of the 2‐, 4‐, and 6‐(phenylmethyl)‐3‐methylpyridines, and the 3‐[2‐, 3‐, and 4‐(methylphenylmethyl)]pyridines. These by‐products resulted from the coupling of an arylmethyl fragment with the opposite aryl group. A concerted reaction is suggested for the ortho couplings and a radical rearrangement for the para couplings. Authentic samples of three of these by‐products were prepared for comparison. A similar reduction of (+)‐ N ‐nitroso‐3‐[(phenylethylamino)methyl]pyridine gave (+)3‐(2‐phenylpropyl)pyridine of undetermined optical purity and by‐products which were not examined but whose nmr spectrum indicated them to be of analogous origin.