Campus Access Only
All rights reserved. This publication is intended for use solely by faculty, students, and staff of University of the Pacific. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, now known or later developed, including but not limited to photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or the publisher.
Date of Award
1972
Document Type
Thesis
Degree Name
Master of Science (M.S.)
Department
Graduate School
First Advisor
Emensdy
First Committee Member
Donald K wedegaertna
Second Committee Member
Charlie A
Abstract
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 then trans-2. These results neither clearly establish nor rule out acetoxyl participation in the rear- rangement of trans-1
Pages
61
Recommended Citation
Lewis, Virginia Hill. (1972). The study of the isomerization of trans-3-acetoxy-2-bromocyclooctene. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/1767
Rights Statement
No Known Copyright. URI: http://rightsstatements.org/vocab/NKC/1.0/
The organization that has made the Item available reasonably believes that the Item is not restricted by copyright or related rights, but a conclusive determination could not be made. Please refer to the organization that has made the Item available for more information. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use.
