Tetrahedron p. 1069 - 1074 (1983)
Update date:2022-08-11
Topics:
Davidson, R. Stephen
Goodwin, Dean
Pratt, Julie E.
A variety of α-oxo-carboxylic esters are shown to undergo direct photo-oxidation, in both polar and non-polar solvents, to produce a higher yield of carbon dioxyde than under degassed conditions.In the case of n-hexyl pyruvate, hexaldehyde is also a product of the reaction.Evidence is presented which indicates that singlet oxygen plays little, if any, part in these decarboxylations.A mechanism involving electron transfer from the excited α-oxo-carboxylic ester to ground state oxygen, leading to per-acid intermediates, is proposed as being in competition with the TYpe II process for fragmentation of these esters.
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Doi:10.1021/j100199a037
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