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(2+4)-Cycloaddition with Singlet Oxygen. 17O-lnvestigation of the Reactivity of Furfuryl Alcohol Endoperoxide¶
Authors:Andr M Braun  Hans Dahn  Ernst Gassmann  Ioannis Gerothanassis  Laurent Jakob  Jordanka Kateva  Claudia G Martinez  Esther Oliveros
Institution:André M. Braun,Hans Dahn,Ernst Gassmann,Ioannis Gerothanassis,Laurent Jakob,Jordanka Kateva,Claudia G. Martinez,Esther Oliveros
Abstract:In earlier work, the use of furfuryl alcohol as a specific singlet oxygen acceptor was proposed because of the high ratio between the rate constants of chemical reaction and physical quenching. In contrast to furfuryl aldehyde, a number of products are formed by this type II photo-oxidation of furfuryl alcohol. These products may be derived from the endoperoxide of furfuryl alcohol as a common intermediate. The present work focuses on the reactivity of this endoperoxide that was marked specifically by the use of 17O2 as a source for singlet oxygen. The analyses of the stable products, their yields and their labeling distribution reveal a strong solvent effect on the primary reaction pathways, and nucleophilic substitution reactions leading to hydroperoxide intermediates are dominant.
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