Reactivity of acyclic (pentadienyl)iron(1+) cations with phosphorous-stabilized carbon nucleophiles and with nitrogen nucleophiles
by Ma, Yuzhi, M.S., MARQUETTE UNIVERSITY, 2011, 67 pages; 1490934

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 divinylcyclopropane carboxylates can form cycloheptadiene.

The reacivity 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 azide with terminal alkynes.

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

 
AdviserWilliam A. Donaldson
SchoolMARQUETTE UNIVERSITY
SourceMAI/ 49-05, p. , May 2011
Source TypeThesis
SubjectsOrganic chemistry
Publication Number1490934
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