(1-Adamantanethio)pyridines and tetrahydropyridines from the reaction of 1-adamantanethiol with pyridine I-oxide in acetic anhydride

Autor:	Bernard A. Mikrut, Pamela Y. P. Chan, Krishan K. Khullar, Ludwig Bauer, Richard S. Egan, John M. Kokosa
Rok vydání:	1974
Předmět:	chemistry.chemical_compound Acetic anhydride 1-adamantanethiol Column chromatography chemistry Proton Organic Chemistry Pyridine Polymer chemistry Oxide Mass spectrum Organic chemistry Hydrochloric acid
Zdroj:	Journal of Heterocyclic Chemistry. 11:713-718
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570110509
Popis:	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.
Databáze:	OpenAIRE
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