Date of Award

Spring 2011

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Donaldson, William A.

Second Advisor

Yi, Chae S.

Third Advisor

Fiedler, Adam

Abstract

A lot of studies regard organoiron compounds have been made in recent years.Nucleophilic addition with soft nucleophiles such as malonate anions or phosphonatestabilized carbon nucleophiles, or harder nucleophiles such as organolithium or Grignardreagents to an acyclic (pentadienyl)iron cation results in the (pentenediyl)iron complexes.

Reaction of (pentadienyl)iron complexes with paraformaldehyde via Horner-Emmonsolefination will give enolate complex. Oxidation of the enolate leads to the formation ofcyclopropane carboxylates. Further oxidation of divinylcyclopropane carboxylates canform cycloheptadiene.

The reacivity of acyclic (pentadienyl)iron cations with nitrogen nucleophiles such aspotassium phthalimide were examined, which could be used as potential routes tosynthesis natural product. "Click chemistry" was also introduced to see the reactivity oforganoiron azide with terminal alkynes.

We have also proposed to synthesize a model of bicycle [4,1,0] heptanes via the ringclosing metathesis of vinylcyclopropanes.

COinS