期刊
TETRAHEDRON
卷 67, 期 7, 页码 1406-1421出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.12.057
关键词
Electron donor acceptor; Electrochemisty; Spectroelectrochemistry; Electron transfer; Ferrocene; Naphthaquinones; Thermal rearrangement
资金
- Scientific and Technical Research Council of Turkey [TBAG-107T811, 109T025]
- Research Board of Istanbul Technical University [BAP-32464]
- FABED Foundation
A practical approach to ferrocenyl naphthaquinone derivatives involving thermal rearrangement of variously substituted 4-aryl-4-hydroxycyclobutenones was described. The reaction of 3-ferrocenyl-4-isopropoxy-3-cyclobutene-1,2-dione with different aryl lithiums gave the corresponding 4-aryl-4-hydroxycyclobutenones, which were heated in p-xylene at reflux open to the air to yield ferrocenyl naphthaquinones. The redox chemistry of the ferrocenyl naphthaquinones was studied by electrochemical and in situ spectroelectrochemical techniques in CH2Cl2 solution and in CH3CN solution with water, weak and strong acidic additives. Ferrocenyl naphthaquinones displayed reversible two reduction processes involving semiquinone radical anion (Fc-snq(center dot-)), dianion (Fc-nq(2-)) species and a one-electron oxidation process based on the ferrocenium/ferrocene (Fc(+)-nq/Fc-nq) couple in CH2Cl2. The redox reaction mechanism of the ferrocenyl naphthaquinones in the presence of the additives proceeded via hydrogen bonding or proton-coupled electron transfer. Effects of the substituents on the reduction potentials and intramolecular charge-transfer bands of ferrocenyl naphthaquinones were also discussed. (C) 2011 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据