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Paper | Regular issue | Vol 63, No. 9, 2004, pp.2051-2056
Published online, 30th July, 2004
DOI: 10.3987/COM-04-10155
Formation of a Sixteen-membered Ring by Condensation of N,N ’-Dimesityl-propane-1,3-diamine with Triethyl Orthoformate and Ammonium Tetrafluoroborate

Andreas L. Paulsen and Robert Madsen*

*Department of Chemistry, Building 201, Technical University of Denmark, DK-2800 Lyngby, Denmark

Abstract

Cyclocondensation of N,N’-dimesityl-propane-1,3-diamine with triethyl orthoformate and ammonium tetrafluoroborate gave as the major product macrocycle (2) under neat conditions and 1,3-dimesityl-3,4,5,6,-tetrahydro-pyrimidin-1-ium tetrafluoroborate with ethanol as the solvent. The structures of the two ring systems were confirmed by X-Ray diffraction analysis.