Journal of Organic Chemistry p. 6836 - 6839 (1991)
Update date:2022-08-10
Topics:
Luchetti, Luciana
Rosnati, Vittorio
The Clemmensen reduction of acetophenone and related substrates (PhCHXCH3, X = Cl, OH, OAc) was investigated in anhyd AcOH and in the presence of LiCl, HCl, or TFA.Ethylbenzene, 1-acetoxy-1-phenylethane, 2,3-diphenyl-2,3-butanediol, and 2,3-diphenyl-2-butene were formed in yields strongly dependent on the experimental conditions.The formation of the hydrocarbon was favored in neat AcOH and in AcOH/HCl/LiCl.Ionic and nonionic pathways were recognized.In the presence of Cl-, the proposed mechanism involves the intermediacy of PhCH(CH3)Cl.The process may proceed via
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