Graduate Thesis Or Dissertation
 

Formation of alkyl-and dialkylcarbenes. The 3-cyclohexenyl carbinyl carbene system

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  • The 3-cyclohexenyl carbinyl carbene species was formed by the thermal decomposition of the p-toluenesulfonylhydrazone sodium salt and by oxidation of the hydrazone. Several oxidizing agents were studied. The products were investigated under aprotic and protic conditions and at various temperatures. The diazocompound was formed as an intermediate and found to be relatively stable although extremely sensitive to the conditions. When the diazocompound was decomposed, the azine and the hydrocarbon products, both major and minor, were characterized. Under aprotic conditions the hydrocarbon yield was small and showed a large amount of β-insertion. The β- to γ- insertion ratio decreased as the system became protic. A comparison of the two methods of carbene formation is presented.
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