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UBC Theses and Dissertations

Remote oxidation of cyclic and acyclic esters Ma, Chun-Leung

Abstract

The oxidation of octadecyl acetate (97; n=l6), dodecyl acetate (97; n=10), tetradecyl acetate (97; n = 12), hexadecyl acetate (97; n = 14) and docosyl acetate (97; n=20) by chromium trioxide in glacial acetic acid/acetic anhydride to a mixture of mono-oxo-acetates and the method used to determine the relative amounts of isomeric oxo-acetates present in the product mixture, is described. Evidence is given for the validity of the analytical method to estimate the relative amounts of isomeric oxo-acetates. Subseguent conversion of the mixture of mono-oxo-hexadecy1 acetates (98; x+y=13)> mono-oxo-dodecyl acetates (98; x+y=l9), and mono-oxo-tetradecyl acetates (98; x+y=1l) to the corresponding mixture of mono-unsaturated acetates is described. These compounds are considered to be sex pheromones for the bertha armyworm, oak leaf rodler moth and some fruit moths respectively. The oxidation of 16-hexadecano1ide (117 ; n = 15), 15-pentadecanolide (117; n = 14) and 12-dodecanolide (117; n =11) by chromium trioxide in glacial acetic acid/acetic anhydride to a mixture of mono-oxo-1actones and the method employed to determine the relative amounts of isomeric mono-oxo-1actones present in the product mixture, is reported. Subsequent conversion of the mixture of mono-oxo-16-hexadecanolides (118; x+y=14) to the mixture of mono-unsaturated hexadecano1ides (123; a+b=13) has been achieved. The latter mixture is believed to be part of the sex pheromone of the oak leaf roller moth. The oxidation of cyclopentadecyl acetate (135) and cyclotridecyl acetate (145) by chromium trioxide in glacial acetic acid/acetic anhydride to a mixture of mono-oxo-cyclic acetates and the method used to identify and determine the relative amounts of isomeric cyclic oxo-acetates, is described.

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