Graduate Thesis Or Dissertation

 

Some synthetic efforts in small ring chemistry Public Deposited

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https://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/np193d05r

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  • Cyclopropylcyclobutene was prepared via the intermediate dicyclopropylcarbinyl carbene which was generated by the thermal decomposition of the sodium salt of dicyclopropylketone p-toluenesulfonylhydrazone. The successive thermal isomerization of cyclopropylcyclobutene to 2-cyclopropyl-1, 3-butadiene and to vinylcyclopentene was studied. Kinetic data were obtained for the cyclopropylcyclobutene to 2-cyclopropyl-1, 3-butadiene isomerization in the gas phase. Decomposition of the sodium salt was studied in different solvent systems at 130°, but bicyclo(1.1.0)butane ring formation was not a major reaction pathway under conditions similar to those used in the decomposition of cyclopropylcarboxaldehyde p-toluenesulfonylhydrazone. Attempts to synthesize the compounds bicyclo-(2.2.0)hex-1(4)-ene and bicyclo(2.2.0)hex-1-ene via carbenoid intermediates were hampered by difficulties in preparing the necessary precursors.
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