Abstract
Singlet oxygen reacts with 2,3-dihydrofuran, 5-methyl-, 4,5-dimethyl-, and 4-carbomethoxy-5-methyl-2,3-dihydrofuran, 5,6-dimethyl-3,4-dihydro-2H-pyran, and 3-methoxy-2-methyl-2-butene (32) in nonpolar and polar aprotic solvents to yield dioxetanes and allylic hydroperoxides, except 32, which gives only allylic hydroperoxides. It is suggested that [2+2] cycloadditions and ene reactions occur via different transition states and intermediates, zwitterions and perepoxides, respectively. Furthermore, the remarkable propensity to dioxetane formationof dihydrofurans compared to that of dihydropyrans and the other enol ethers seems to be due to the rogodoty of the five-membered ring in the transition state and intermediate zwitterion
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