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 phosphonate stabilized carbon nucleophiles, or harder nucleophiles such as organolithium or Grignard reagents to an acyclic (pentadienyl)iron cation results in the (pentenediyl)iron complexes.
Reaction of (pentadienyl)iron complexes with paraformaldehyde via Horner-Emmons olefination will give enolate complex. Oxidation of the enolate leads to the formation of cyclopropane carboxylates. Further oxidation of divinyl cyclopropane carboxylates can form cycloheptadiene.
The reactivity of acyclic (pentadienyl)iron cations with nitrogen nucleophiles such as potassium phthalimide were examined, which could be used as potential routes to synthesis natural product. "Click chemistry" was also introduced to see the reactivity of organoiron aside with terminal alkynes.
We have also proposed to synthesize a model of bicycle [4,1,0] heptanes via the ring closing metathesis of vinyl cyclopropanes.