28698-05-7Relevant academic research and scientific papers
Trifluoromethanesulfonic (Triflic) Acid Catalyzed Transformations of α-Hydroxy Carbonyl Compounds
Olah, George A.,Wu, An-hsiang
, p. 2531 - 2534 (2007/10/02)
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.
α-Heterosubstituted Phosphonate Carbanions. 11. Benzoins via an Acyl Anion Equivalent. Novel One-Pot Preparation of Benzofurans via Benzoins Using Hydriodic Acid
Koenigkramer, Rusty E.,Zimmer, Hans
, p. 3994 - 3998 (2007/10/02)
Diethyl 1-(trimethylsiloxy)-1-phenylmethanephosphonate carbanion 2 is introduced as a novel acyl anion equivalent.When 2 reacts with aldehydes or ketones, a 1,4 oxygen-oxygen silicon migration with subsequent loss of diethyl lithium phosphite is observed.An efficient method utilizing 2 for the preparation of otherwise difficultly obtainable substituted benzoins is presented.Also a novel one-pot method which offers a facile entry into the 2-phenylbenzofuran ring system from 2 via benzoin intermediates using hydriodic acid was developed.
α-HETEROSUBSTITUTED PHOSPHONATE CARBANIONS IX : DIETHYL 1-PHENYL-1-TRIMETHYLSILOXYMETHANE PHOSPHONATE AS AN ACYL ANION EQUIVALENT; A NOVEL METHOD FOR THE PREPARATION OF α-HYDROXYKETONES.
Koenigkramer, Rusty E.,Zimmer, Hans
, p. 1017 - 1020 (2007/10/02)
Diethyl 1-phenyl-1-trimethylsiloxymethane phosphonate carbanion was found to react as an effective acyl anion equivalent in the preparation of α-hydroxy ketones from aliphatic and aromatic aldehydes and ketones.A 1,4-oxygen-oxygen silicon migration was also observed.
