Date of Award

2015

Degree Name

Chemistry

College

College of Science

Type of Degree

M.S.

Document Type

Thesis

First Advisor

Michael Castellani

Second Advisor

John Hubbard

Third Advisor

Robert Morgan

Abstract

Metallocenophanes are divided into two categories, monomolecular metallocenophanes and bimolecular metallocenophanes. This project focused on monomolecular metallocenophanes, in this case where a carbon-based bridge links the two cyclopentadienyl rings of a metallocene. Previous metallocenophanes were prepared by harsh methods and only work to form ferrocenophanes. Therefore, a new method was utilized to synthesize ferrocenophanes that should allow Co, Cr, Mn, Ni, V derivatives to be prepared. This thesis reports the syntheses of four molecules, 1,4-bis(tetramethylcyclopentadienyl)butane, 1,5-bis(tetramethylcyclo-pentadienyl)- pentane, 1,4-bis(cyclopentadienyl)butane, and 1,5-bis(cyclopentadienyl)pentane by utilizing two different methods in 71%, 69%, 98%, and 90% yields, respectively. These four molecules were deprotonated by BuLi, and ultimately reacted with FeCl2•1.5(THF) to obtain [4]octamethylferrocenophane (50%), [5]octamethylferrocenophane (54%), [4]ferrocenophane (34%), and [5]ferrocenophane (28%). The identities of the ferrocenophanes were verified by 1H NMR spectroscopy.

Subject(s)

Unimolecular reactions.

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