Hydroperoxide and endoperoxide lactones from photooxygenation of 3-alkylidenedihydrofuran-2,4-diones |
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Authors: | Schobert Rainer Stehle Ralf Milius Wolfgang |
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Affiliation: | Chemisches Laboratorium der Universit?t, Universit?tsstrasse 30, NW I, 95440 Bayreuth, Germany. rainer.schobert@uni-bayreuth.de |
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Abstract: | 3-Alkylidenedihydrofuran-2,4-diones 1 can be photooxygenated with O(2)/TBHP to hydroperoxides 3 which slowly decompose to diols 5. Stable endoperoxides 4 are best prepared by photooxygenation of 1 with 2 equiv of O(2) in the presence of CuSO(4) and p-TosOH following a nonradical mechanism. They are rapidly reduced by anhydrous FeBr(2) to give butenolide 9 indicating a potential antimalarial activity. |
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