Graduate Thesis Or Dissertation
 

Cyclization of organolithium and -zirconium compounds ; Rearrangements of selected anionic compounds in highly disassociative solvents

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  • Intramolecular cyclization of organometallic compounds represents a promising tool for synthesis. The reaction involves exothermic consumption of intramolecular double bonds via insertion into a carbon metal sigma bond. This represents an intramolecular example of the reaction type responsible for metal catalyzed polymerization of olefins. Organolithium reagents were found to cyclize forming monoand bicyclic compounds stereospecifically in average yields. The organolithium reagents were prepared by the reaction of alkenyl halides with lithium metal or radical anions. Zirconocene was found to effect carbocyclization of simple dienes forming 5- and 6-membered carbocycles. The stereochemistry of the elimination of hydrogen chloride from 2-benzylchlorocyclopropane when treated with a strong base forming E-1-pheny1-1, 3-butadiene was found to be stereochemically consistent with that of the thermally allowed opening of halocyclopropanes. The potassium salt of 6, 6- dimethy1-2, 4-cyclohexdien-l-ol was found to undergo a [1,5] hydrogen shift at 65° when dissolved in hexamethylphosphoramide (HMPT) producing 6, 6- dimethy1-3-cyclohexen- l-one when neutralized.
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