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http://hdl.handle.net/11375/29974
Title: | PYROLYTIC DECOMPOSITION OF ALLYLIC ESTERS |
Authors: | Lan, Leo Ka-Ming |
Advisor: | Warkentin, J. |
Department: | Chemistry |
Keywords: | Chemistry |
Abstract: | The acetate of 6,6-dimethyl-2-cyclohexen-l-ol was thermally decomposed and the pyrolysis products were characterized. This allylic ester decomposed with difficulty. Under conditions which led to complete decomposition of 3-acctoxycyclohexene, 6,6-dimethyl-2-cyclohexen-l-ol acetate was virtually unreacted. Complote decomposition of the allylic acetate was achieved at about 600oC. The pyrolysis products consisted mainly of o-xylene, toluene, 5,5-dimethyl-1,3-cyclohexadiene and acetic acid. The aromatic compounds are thought to be formed from the less stable dione. Partial decomposition of ester enriched with deuterium in the 4-position, permitted estimation of the isotope effect, kH/kD, for the pyrolytic elimination. Tne value obtained was about 2. Together with other experimental evidence, it indicates that the main mode of decomposition is 1,4-conjugate elimination and that allylic rearrangement, if it occurs at all, is unimportant. |
URI: | http://hdl.handle.net/11375/29974 |
Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Lam_Leo_K_1963Sept_masters.pdf | 1.53 MB | Adobe PDF | View/Open |
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