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, cilt.14, sa.1, ss.82-87, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 14 Sayı: 1
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1002/hc.10088
  • Dergi Adı: HETEROATOM CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.82-87
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.