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

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.