Siloxy-cope rearrangements of the trans-l-vinylcyclotridec-3-en-l-ol system Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/z890rz02k

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  • The thermolysis of trans-1 -trimethylsiloxy- 1-vinylcyclotridec- 3-ene (VI-OTMS) led to the formation of two major products: 4-vinylcyclotridecanone (VII) and cyclopentadec-5-en-l-one (VIII) after hydrolysis. Ketone VII is produced by a concerted [3, 3] sigmatropic shift, while ketone VIII is formed by a [1, 3] sigmatropic shift with a concerted or diradical mechanism. The rates of reaction and activation parameters have been determined. The large amount of [3, 3] shift product formed hinders the use of the siloxy-Cope rearrangement as a two-carbon ring expansion reaction for the thirteen member ring systems. The synthetic scheme for the formation of 1-vinylcyclotridec- 3-ene-l-ol produces only the trans-isomer.
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