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1,1′,3,3′-Tetraalkyl-2,2′-biperimidinylidenes: Unexpected substituent effects on the reactivity of carbon–carbon double bond

✍ Scribed by Bülent Alıcı; Tuncer Hökelek; Engin Çetinkaya; Bekir Çetinkaya

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 109 KB
Volume: 14
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.10088

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✦ Synopsis

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. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:82–87, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10088

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