Tetrahedron

Singlet oxygen photooxygenation of furans: Isolation and reactions of (4+ 2)-cycloaddition products (unsaturated sec.-ozonides)

K Gollnick, A Griesbeck

Index: Gollnick, Klaus; Griesbeck, Axel Tetrahedron, 1985 , vol. 41, # 11 p. 2057 - 2068

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Citation Number: 187

Abstract

Tetraphenylporphin-photosensitized oxygenations of furan (19), 2-methylfuran (26), 2- ethylfuran (39), furfurylalcohol (24), 2-acetylfuran (40), 2-methoxyfuran (42), 2, 5- dimethylfuran (30), furfural (25) and 5-methylfurfural (41) in non-polar aprotic solvents yield the corresponding monomeric unsaturated secondary ozonides due to a (4+ 2)- cycloaddition of singlet oxygen to these furans. With the exception of the ozonide derived ...