Hydroperoxide and endoperoxide lactones from photooxygenation of 3-alkylidenedihydrofuran-2,4-diones.
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.
Schobert
Rainer
R
Chemisches Laboratorium der Universität, Universitätsstrasse 30, NW I, 95440 Bayreuth, Germany. rainer.schobert@uni-bayreuth.de
Stehle
Ralf
R
Milius
Wolfgang
W
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000475:Alkenes / Q000737:chemistry*; D000962:Antimalarials / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*; D010777:Photochemistry
D000475:Alkenes; D000962:Antimalarials; D005663:Furans; D007783:Lactones; D010545:Peroxides; C004511:butenolide; D006861:Hydrogen Peroxide; D015107:4-Butyrolactone