Tetrahedron letters

Photooxygenation of tetramethylallene competing (2+ 2) cycloaddition and ene-reactions with singlet oxygen

K Gollnick, A Schnatterer

Index: Gollnick, Klaus; Schnatterer, Albert Tetrahedron Letters, 1985 , vol. 26, # 41 p. 5029 - 5032

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Citation Number: 9

Abstract

Abstract TPP-sensitized photooxygenation of tetramethylallene (4) in carbon tetrachloride yields acetone (5), 2, 4-dimethyl-4-hydroxy-1-penten-3-one (8) and 2, 4-dimethyl-1, 4- pentadien-3-one (9) in a ratio of 35: 20: 45, besides minor amounts of resinous products and carbon dioxide. Isomerization of 4 to 2, 4-dimethyl-1, 3-pentadiene (6) does not occur under the reaction conditions. DABCO quenches the photooxygenation, whereas 2, 4, 6-tri-t- ...

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