The Journal of Organic Chemistry

Dye-sensitized photooxygenation of 2, 3-dihydrofurans: competing [2+ 2] cycloadditions and ene reactions of singlet oxygen with a rigid cyclic enol ether system

K Gollnick, K Knutzen-Mies

Index: Gollnick, Klaus; Knutzen-Mies, Karen Journal of Organic Chemistry, 1991 , vol. 56, # 12 p. 4017 - 4027

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Citation Number: 43

Abstract

Singlet oxygen reacts with 2, 3-dihydrofuran (l), 5-methyl-(7), 4, bdimethyl-(131, and 4- carbomethoxy-5-methyl-2, 3-dihydrofuran (20), 5, 6-dimethyl-3, 4-dihydro-2iY-pyran (26), 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. The dioxetanes were isolated, but decompose slowly with weak chemiluminescence at ...