C-2 deprotonation of 1,3-dibutylperimidinium bromide (1a) with sodium hydride and a catalytic amount of potassium tert-butoxide in dry THF led to the formation of the exceptionally inert tetraaminoalkene 2a. In contrast, isostructural tetrakis(2-methoxyethyl)-tetraaminoalkene (2b) instantaneously reacted with O-2 to yield urea 3b, and silver nitrate was readily reduced with 2b to form a silver mirror. Compound 2a has been characterized by X-ray diffraction studies; the naphtho-pyrimidine skeleton imposes structural constraints and some rigidity to the C=C bonding. (C) 2003 Wiley Periodicals, Inc.
C1 Ege Univ, Dept Chem, TR-35100 Bornova, Turkey.
Hacettepe Univ, Dept Phys, TR-06532 Ankara, Turkey.
Inonu Univ, Dept Chem, TR-44069 Malatya, Turkey.