Trifluoromethanesulfonic (Triflic) Acid Catalyzed Transformations of α-Hydroxy Carbonyl Compounds

DOI: 10.1021/jo00007a048

Source and publish data:

Journal of Organic Chemistry p. 2531 - 2534 (1991)

Update date:2022-08-04

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Authors:

Olah, George A.

Wu, An-hsiang

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Article abstract of DOI:10.1021/jo00007a048

Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantanone.Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione.Reactions of a series of α-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively.The reactions and their suggested mechanism are discussed.

Full text of DOI:10.1021/jo00007a048

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