Ring transformations of heterocyclic halogeno compounds with nucleophiles. 39

J.P. Geerts, H.C. van der Plas

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14 Citations (Scopus)


Treatment of 4-chloro-2-dimethylaminopyrimidine (1a) and its 5-phenyl derivative (1b) with potassium amide in liquid ammonia and subsequent workup of the reaction mixtures lead to the formation of 2-dimethylamino-4-methyl-s-triazine and 4-benzyl-2-dimethylamino-s-triazine, respectively. By extensive 13C NMR investigations of both reaction mixtures in liquid ammonia containing potassium amide, a number of unstable intermediates could be identified: from 1a the 1:1 anionic σ complex 2a and the anionic open-chain intermediate aminoethynyldiazabutadiene 3; from 1b, the σ complex 2b and the anionic aminodiazabutadiene 7, but also a redox product of 7, i.e., the cyanoaminoazabutadiene 8. Based upon the results of a deuterium labeling experiment it is assumed that the conversion of 7 into 8 occurs by an intramolecular oxidation-reduction process.
Original languageEnglish
Pages (from-to)2682-2685
JournalJournal of Organic Chemistry
Issue number13
Publication statusPublished - 1978


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