Photoisomerization of bicyclooctanones in solution

Critch, Susan Clift (1975) Photoisomerization of bicyclooctanones in solution. Masters thesis, Memorial University of Newfoundland.

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    Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
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Abstract

The photolysis of bicyclo(3.2.1)octan-2-one (XVII), bicyclo(2.2.2)octan-2-one (XXV), and 1,8,8-trimethyl-bicyclo(3.2.1)octan-2-one (homocamphor) (IX) in nucleophilic solvents (methanol, water, cyclohexylamine) is reported. The structures of the products were established by synthesis and comparison with authentic materials, and, in the case of XVII, the two aldehydes (XVIII, XIX) were isolated and the position of the double bond established by nuclear magnetic resonance shift measurements and confirmed by degradation. The spectroscopic properties of the products were recorded. -- The photochemical products were predominantly derived from aldehydes and ketenes and the product ratios are tabulated. The results are rationalized in terms of conformational analysis of the diradical intermediates involved. A potential general method of altering the product ratio using cyclohexylamine is described, as are various synthetic approaches to these ketones.

Item Type: Thesis (Masters)
URI: http://research.library.mun.ca/id/eprint/7310
Item ID: 7310
Additional Information: Bibliography: leaves 93-102.
Department(s): Science, Faculty of > Chemistry
Date: 1975
Date Type: Submission
Library of Congress Subject Heading: Bicyclooctanones;Isomerization;

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