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Synthesis 2009(16): 2773-2777  
DOI: 10.1055/s-0029-1217601
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Electrochemical Signature of Novel Norbornyl-ferrocene Hybrids

Faiz Ahmed Khan*, Sarasij K. Upadhyay
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India
Fax: +91(512)2597436; e-Mail: faiz@iitk.ac.in;
Further Information

Publication History

Received 2 March 2009
Publication Date:
10 July 2009 (online)

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Abstract

Novel norbornyl-ferrocene hybrids have been synthesized in excellent yields via Diels-Alder reactions between 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene and vinyl- or acryloylferrocenes. Halogen reduction of vinylferrocene adducts followed by catalytic hydrogenation afforded ferrocenyl-norbornane. Hybrids showed the dependence of the redox potential on the nature of the substituents on the norbornyl moiety.

Key words

Diels-Alder reaction - ferrocene - radical hydrodehalogenation - reduction - electrochemical study

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