Photosensitized oxygenation of α-pyran(l) (2,5,5,8a-tetramethyl-6,7,8,8a-tetrahydro-5H- l-benzopyran), in methanol using rose bengal, rapidly formed a stable peroxide (2). The peroxide (2) gave 6,6-dimethyl-8-undecene-2,7,10-trione(11) at 140°C in xylene, and 8(or 9)-methoxy or hydroxy derivatives of 6,6-dimethyl-undecane-2,7,10-trione (12a or b) by hydrochloric acid. These triketones (11 and 12a) were also obtained by a photo-reaction from the peroxide(2).
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Etoh et al. (1973) studied this question.