Physical Sciences and Mathematics Commons^™

The Study Of The Isomerization Of Trans-3-Acetoxy-2-Bromocyclooctene, Virginia Hill Lewis

University of the Pacific Theses and Dissertations

The isomerization of trans-3-acetoxy-2-bromocyclooctene (trans-1) to cis-3-acetoxy-2-bromocyclooctene (cis-1) was studied, trans-3- Methoxy-2-bromocyclooctene (trans-2) was used as a model compound for comparison. The rate of isomerization of both compounds increased tremendously with iodine (free radical catalysis) and decresed tremendously in the presence of hydroquinone (free radical inhibitor). This showed that the isomerizations of trans-1 and trans-2 are free radical catalyzed. It was anticipated that acetoxyl participation in trans-1, by stabilizing the free radical intermediate, would cause the rate of rearrangement of trans-1 to be much greater than the rate of rearrangement of trans-2. However, trans-1 iscented only about four times faster …