33484-95-6Relevant academic research and scientific papers
Reactivity of the secondary benzylic Grignard reagent from 1-phenylethyl chloride with aldehydes and ketones. More evidence for the rearrangement mechanism in benzyl Grignard reactions
Bernardon, Claude
, p. 11 - 18 (2007/10/02)
Additional evidence for the mechanism proposed previously to account for diol formation in the reaction of the Grignard reagent from benzyl chloride with aldehydes has been obtained from a study of the interaction of the Grignard reagent from 1-phenylethyl chloride with carbonyl compounds.This Grignard reagent reacts with ketones (except non-enolisable ketones) to give normal alcohols in low yields, and with aldehydes to give diols.However, in contrast to that formed in the reaction of benzylmagnesium chloride, an unstable trienic alcohol formed from the rearrangement of the corresponding alkoxide could be isolated in some case as the major product, providing confirmatory evidence for the existence of an initial reversible rearrangement in the reaction of the benzylic Grignard reagents with carbonyl compounds.
Stereoselectivity in the Condensation Reactions of 1-Phenylethyl Alkyl and Phenyl Ketones with Organometallic Reagents
Alvarez-Ibarra, Carlos,Arjona, Odon,Perez-Ossorio, Rafael,Perez-Rubalcaba, Alfredo,Quiroga, Maria L.,Santesmases, Maria J.
, p. 1645 - 1648 (2007/10/02)
Stereochemical results of the condensation reactions of a series of ketones, PhCHMeCOR (R= Me, Et, Pri, But, Ph), with various organomagnesium and organolithium derivatives in ethers as solvents are reported.Results are accounted for on the basis of competition between two transition states which may adopt either Karabatsos- or Felkin-type conformations according to the nature of R, the reagent nucleophilicity, and the polarity of solvent.Polar and steric analysis of this reaction allows highly stereoselective syntheses of diastereoisomeric α-phenylalkanols to be devised.
