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Isotope exchange of active methyl hydrogens. III. Preparation of 2, 4, 6-tri-d3-methylpyridine, 3, 5-di-d3-methylphenol, 3, 5-di-d3-methyl-2-acetylfuran, and 4, 6, 8-tri-d3-methylazulene, from 2, 4, 6-tri-d3-methylpyrylum perchlorate

✍ Scribed by A. T. Balaban; E. Gǎrd; A. Vasilescu; A. Barabas

Publisher: John Wiley and Sons
Year: 1965
Tongue: French
Weight: 361 KB
Volume: 1
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2590010403

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✦ Synopsis

From 2,4,6-tri-da-methylpyryliurn perchlorate the title compounds II-V were obtained by reaction with aqueous or gaseous ammonia, aqueous sodium hydroxide, aqueous hydrogen peroxide and sodium cyclopentadienide, respectively. The preparation of II-IV in aqueous solution proves that the nucleophilic additions to the pyrylium ring proceed faster than the dedeuteration. Infrared and nuclear magnetic resonance spectra of these compounds confirm that their methyl groups are deuterated.

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