Singlet oxygen oxygenation of enol ethers; the synthesis of optically active 1,2-dioxetanes. II

(+)-(Methoxymethylene)fenchane I (R = H, R1 = OMe) on singlet O oxidn. gave dioxetanes II and III, which on thermal decompn. underwent chemiluminescence in which (+)-fenchone was the only chemiluminescent species at lmax 420 nm. Photosensitized oxygenation of I (R = OMe, R1 = H) also gave 2 isomeric 1,2-dioxetanes. I were prepd. by Wittig methoxymethylenation of (+)-fenchone. Adamantanone (IV) on Wittig methoxymethylenation, followed by singlet O oxidn. gave dioxetane V, which on thermal decompn. gave only IV and HCO2Me and a bright blue chemiluminescence with lmax 420 nm and k1 2.96 * 10-3 s-1 at 79.9 Deg in decane. The prepn. of the dioxetanes allows the comparison of light- and chem. induced circular polarization of luminescence. [on SciFinder (R)