Journal of Organic Chemistry p. 953 - 955 (1992)
Update date:2022-08-10
Topics:
Adam, Waldemar
Asensio, Gregorio
Curci, Ruggero
Gonzalez-Nunez, Maria Elena
Mello, Rosella
The efficient conversion of (R)-(-)-2-phenylbutane <(-)-1> into (S)-(-)-2-phenyl-2-butanol <(-)-2> with high configurational retention was achieved under remarkably mild conditions by using methyl(trifluoromethyl)dioxirane (3a).The Arrhenius actication parameters were determined by using methyl(trifluoromethyl)dioxirane (3a) in solution of 1,1,1-trifluoropropanone (TFP) or methylene chloride.A significantly lower activation energy was determined for the oxyfunctionalization of (+/-)-1 by 3a in the less polar methylene chloride.An ordered transition state I is proposed for this regio- and stereoselective O atom insertion into the benzylic C-H bond of hydrocarbon (-)-1.
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