The Invention of Radical Reactions. Part XXI. Simple Methods for the Radical Deoxygenation of Primary Alcohols.

DOI: 10.1016/S0040-4020(01)86502-9

Source and publish data:

Tetrahedron p. 8969 - 8984 (1991)

Update date:2022-08-05

Topics:

Authors:

Barton, Derek H. R.

Blundell, Paul

Dorchak, Joseph

Jang, Doo Ok

Jaszberenyi, Joseph Cs.

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Article abstract of DOI:10.1016/S0040-4020(01)86502-9

Novel radical-chain deoxygenations of primary alcohols are described.The alcohols are acylated with the reagents pentafluorophenyl chlorothionoformate, 2,4,6-trichlorophenyl chlorothionoformate and 4-fluorophenyl chlorothionoformate and the intermediate thionocarbonates are deoxygenated with tributyltin hydride, triphenylsilane, diphenylsilane or phenylsilane in high-yielding reactions.Key Words: Thionocarbonates, Tributyltin hydride, Triphenylsilane, Diphenylsilane, Phenylsilane, Radical deoxygenations.

Full text of DOI:10.1016/S0040-4020(01)86502-9

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