Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2004, Issue 8, Pages 1774-1780Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200300765
Keywords
enynes; cyanines; cross-coupling; electrochemistry; cyclic voltammetry
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A bis(enediyne) system utilizing anthraquinodimethane as a platform for a redox-active substructure that bears azulenes as pi-electron-accepting groups at the periphery has been prepared by a simple one-pot reaction involving repeated Pd-catalyzed alkynylation of 6-bromoazulenes with the bis(enediyne). The novel bis(enediyne)s exhibited two, one-step two-electron redox properties under electrochemical reduction conditions together with a significant color change owing to the generation of a closed-shell cyanine-type substructure by the two-electron reduction. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
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