Photosensitized oxygenation of alkyl-substituted furans

doi:10.1016/0040-4020(67)85123-8

Tetrahedron

Volume 23, Issue 6, 1967, Pages 2583-2599

https://doi.org/10.1016/0040-4020(67)85123-8 Get rights and content

Abstract

Photooxidation in methanol of 2-methyl-, 2,5-dimethyl-, dicyclohexano- and menthofuran, sensitized by Rose Bengal, produces crystalline 2-methoxy-5-hydroxyperoxy-2,5-dihydrofuran derivatives by addition of solvent to intermediate ozonide-like peroxides.

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^☆: Taken in part from the doctoral disserations of K.-H. Schulte-Elte, Universität Göttingen (1960), and S. Wexler, University of California, Los Angeles (1966). Support from the National Science Foundation (Grants G-25086 and GP-3358) and from the Petroleum Research Fund (administered by the American Chemical Society) is gratefully acknowledged.

¹: Contribution No. 1859

²: Alfred P. Sloan Research Fellow. Part of this work was carried out under a Fulbright Scholarship, 1957–58, at the University of Göttingen, Germany.

³: National Science Foundation Undergraduate Research Participant.

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Photosensitized oxygenation of alkyl-substituted furans☆

Abstract

Angew. Chem.

Chem. Ber.

Angew. Chem.

Angew. Chem.

Angew. Chem.

Liebigs Ann.

C.R. Acad. Sci., Paris

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Org. Chem.

C.R. Acad. Sci., Paris

Liebigs Ann.

J. South African Inst.

Chem. Abstr.

Chem. Ber.

Angew. Chem.

J. Am. Chem. Soc.

Chem. Ber.

Near Infrared Spectroscopy

J. Am. Chem. Soc.

J. Org. Chem.

J. Chem. Soc.

Bull. Soc. Chim. Fr.

Chem. Ber.

Liebigs Ann.

Quart. Rev.