Date of Award

Fall 2008

Document Type

Thesis - Restricted

Degree Name

Master of Science (MS)




Organoiron compounds have been extensively studied. Nucleophilic addition with soft nucleophiles such as malonate anions, or harder nucleophiles such as organolithium or Grignard reagents to an acyclic (pentadienyl)iron cation results in the(pentenediyl)iron complexes. Oxidation of (pentenediyl)iron complexes leads to the formation of cyclopropane carboxylates. Reduction of divinylcyclopropane carboxylate can form cycloheptadienyl methanol. In this way, reaction of the tricarbonyliron cation with prepared 2-(1 ,3-butadienyl)magnesium chloride, followed by oxidative decomplexation, reduction of cyclopropane carboxylates and Cope rearrangement gives 1-vinyl-1 ;4- cycloheptadiene. Diels-Aider [4+2] cycloaddition of 1-vinyl-1 ,4-cycloheptadiene with potent dienophiles (e.g. maleic anhydride, dimethyl acetylenedicarboxylate (DMAD), 4- · phenyl-1 ,2,4-triazoline-3,5-dione (PTAD), dimethyl maleate, 1 ,4-benzoquinone) will afford the bicyclo[5.4.0]undecadienes. It should be noted that reversing the order of decomplexation/Cope rearrangement and Diels-Aider cycloaddition steps results in different bicyclo[5.4.0]undecadienes. Our concentration is on the synthesis of bicyclo[5.4.0]undecadienes by the methods mentioned above. We also proposed to synthesize a model of bis-norxanthanolide. In order to explore the route, mono-iodolactonization of a model cycloheptadiene was examined.


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