Hydroperoxide and endoperoxide lactones from photooxygenation of 3-alkylidenedihydrofuran-2,4-diones.
作者信息
Schobert Rainer, Stehle Ralf, Milius Wolfgang
机构信息
Chemisches Laboratorium der Universität, Universitätsstrasse 30, NW I, 95440 Bayreuth, Germany.
出版信息
J Org Chem. 2003 Dec 12;68(25):9827-30. doi: 10.1021/jo030270a.
PMID:14656117
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.
摘要
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