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(1‐Adamantanethio)pyridines and tetrahydropyridines from the reaction of 1‐adamantanethiol with pyridine I‐oxide in acetic anhydride
Author(s) -
Mikrut Bernard A.,
Khullar Krishan K.,
Chan Pamela Y. P.,
Kokosa John M.,
Bauer Ludwig,
Egan Richard S.
Publication year - 1974
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.5570110509
Subject(s) - chemistry , acetic anhydride , pyridine , hydrochloric acid , pyridine n oxide , acetic acid , pummerer rearrangement , oxide , mass spectrum , organic chemistry , medicinal chemistry , nuclear chemistry , mass spectrometry , chromatography , catalysis
The reaction of pyridine 1‐oxide with 1‐adamantanethiol in acetic anhydride produced a mixture of 2‐ and 3‐(1‐adamantanethio)pyridines, 1‐aeetyl‐2‐(1‐adamantanethio)‐3‐hydroxy‐4‐acetoxy‐1,2,3,4‐telrahydropyridine and the corresponding 3‐acetoxyderivative. Pure substances were separated by means of column chromatography on alumina. The tetrahydropyridines were identified by means of their proton magnetic and mass spectra. 4‐(1‐Adamantanethio)pyridine was synthesized from 4‐chloropyridinc and 1‐adamantanethiol. The three isomeric (1‐adamantanethio)‐pyridines were, each, cleaved by concentrated hydrochloric acid to give 1‐chloroadamantane and the corresponding pyridinethiol.