105420-94-8Relevant articles and documents
(2+4)-Cycloaddition with singlet oxygen. 17O-investigation of the reactivity of furfuryl alcohol endoperoxide
Braun, André M.,Dann, Hans,Gassmann, Ernst,Gerothanassis, Ioannis,Jakob, Laurent,Kateva, Jordanka,Martinez, Claudia G.,Oliveros, Esther
, p. 868 - 874 (2007/10/03)
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 photooxidation 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.
