125741-99-3Relevant academic research and scientific papers
An Efficient Generation of the Aluminum Enolates of 1H-Perfluoroalkyl Ketones from 1-Substituted-1-perfluoroalkenyl Phosphates and Their Aldol Reaction with Aldehydes
Ishihara, Takashi,Kuroboshi, Manabu,Yamaguchi, Koichi,Okada, Yoshiji
, p. 3107 - 3114 (2007/10/02)
Diethyl 1-substituted-1-perfluoroalkenyl phosphates (1), available from perfluoroalkyl ketones and sodium diethyl phosphite, were allowed to react with a reagent derived from lithium aluminum hydride and a metal salt or bromine in tetrahydrofuran below -30 deg C and successively treated with water or aldehydes to give rise to the corresponding 1H-perfluoroalkyl ketones (4) or α-fluoro-α-perfluoroalkyl-β-hydroxy ketones (5), respectively, in moderate to good yields.Copper(II) bromide, copper(I) bromide, and zinc chloride could be employed as the metal salt in the reaction.The phosphates also underwent reductive dephosphorylation with diisobutylaluminum hydride to generate the aluminum enolates of 1H-perfluoroalkyl ketones. 19F NMR analyses indicated that their structure is not an α-metallo ketone but an oxygen-metalated species and that they are appreciably stable below 0 deg C.Treatment with a wide variety of aldehydes at 0 deg C yielded the corresponding aldol products 5 in good to excellent yields, whereas ketones did not react.
Dephosphorylation of 1-Substituted F-1-Alkenyl Phosphates with Diisobutylaluminium Hydride. A New Highly Efficient Method for Generating F-Alkyl Ketone Aluminium(III) Enolates
Ishihara, Takashi,Yamaguchi, Koichi,Kuroboshi, Manabu
, p. 1191 - 1194 (2007/10/02)
1-Substituted F-1-alkenyl phosphates, prepared easily from F-alkyl ketones, were treated with diisobutylaluminium hydride in tetrahydrofuran at 0 deg C for 5 min or at room temperature for 30 min to generate quantitetively the corresponding ketone alumini
