1,1 ',3,3 '-tetraalkyl-2,2 '-biperimidinylidenes: Unexpected substituent effects on the reactivity of carbon-carbon double bond


ALICI B., Hokelek T. , CETINKAYA E., CETINKAYA B.

HETEROATOM CHEMISTRY, vol.14, no.1, pp.82-87, 2003 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 1
  • Publication Date: 2003
  • Doi Number: 10.1002/hc.10088
  • Title of Journal : HETEROATOM CHEMISTRY
  • Page Numbers: pp.82-87

Abstract

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.