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Communication | Regular issue | Vol 55, No. 5, 2001, pp.827-834
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9164
Mesomeric Betainium Salts. Synthesis, X-Ray Analysis, and ESIMS Studies of Tripolar Pyrimidin-4-olates and Pyrimidin-4-aminides

Andreas Schmidt* and Martin Nieger

*Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

Reaction of tetrachloropyrimidine (1) with pyridine in acetone in the presence of sodium iodide yielded the pyrimidin-4-olate (3). Applying analogous reaction conditions to 4-amino substituted 2,5,6-trichloropyrimidine (4a,b) resulted in the formation of bispyridinium salts (5a,b) which yield aminides (6a,b) on deprotonation. As evidenced by means of UV spectroscopy and electron spray MS spectrometry, the title compounds (3) and (6a,b) form π-sandwich complexes in solution.