Oxy-Cope, and Siloxy-Cope rearrangement of cis-1-vinylcyclooct-3-en-1-ol Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/nv9356323

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  • Both oxy-Cope and siloxy-Cope rearrangements involve (1, 3) and (3, 3) sigrnatropic shifts. Both the concerted mechanism, and the stepwise mechanism via a diradical intermediate are possible. In a cyclic system such as cis-l-vinylcyclooct-3-en-l-ol, the thermal rearrangement takes place preferably through a diradical intermediate. At high temperature, the reaction also prefers the diradical mechanism. There are two pathways for the formation of the compounds, cis- and trans-bicyclo(5.3.0)decan-2-one in the oxy-Cope thermal rearrangement. One is directly from the starting compound, cis- 1-vinylcyclooct-3-en-l-ol, and the other is the result of the interconversion from cis- and trans-5-cyclodecenone. This bicyclic compound is not observed in the siloxy-Cope thermal rearrangement. The siloxy Cope thermal rearrangement gives a sizable amount of cis- and trans-l-siloxy-1,2-divinylcyclohexane by (1, 3) shift, and then they rearrange to form the ring expanded products. This trend is not observed in the oxy-Cope rearrangement of cis-Ivinylcyclooct- 3-en-1-ol. The oxy-Cope, and siloxy-Cope rearrangement can be used for synthesis of cyclic, unsaturated ketones, and carbonyl compounds.
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