Syntheses of Arylacetone and Arylacetonitrile by Friedel-Crafts Reaction with α-Chloro-α-(methylthio)-substituted Acetone and Acetonitrile
Novel preparative methods for arylacetone and arylacetonitrile are described.Friedel-Crafts reactions of aromatic compounds with α-chloro-α-(methylthio)acetone (4) and α-chloro-α-(methylthio)acetonitrile (7) in the presence of Lewis acid afforded α-(methylthio)arylacetone (5) and α-(methylthio)arylacetonitrile (8), respectively.Compounds (5) and (8) were converted into the corresponding arylacetone (6) and arylacetonitrile (9) by reduction with zinc dust in acetic acid.Keywords: Friedel-Crafts reaction with α-chloro-α-(methylthio)acetone; Friedel-Crafts reaction with α-chloro-α-(methylthio)acetonitrile; α-(methylthio)arylacetone; α-(methylthio)arylacetonitrile; arylacetone; arylacetonitrile; reductive desulfurization; zinc dust-acetic acid
Tamura, Yasumitsu,Choi, Hong Dae,Mizutani, Masako,Ueda, Yuko,Ishibashi, Hiroyuki
p. 3574 - 3579
(2007/10/02)
Nucleophilic Attack on Olefins Initiated by Dimethyl(methylthio)sulfonium Fluoroborate (DMTSF). Cyanosulfenylation and Oxy- and Oxosulfenylation
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Trost, Barry M.,Shibata, Tohru,Martin, Steven J.
p. 3228 - 3230
(2007/10/02)
Introduction of α-(acyl) methylthiomethyl group into the aromatic ring by Friedel-Crafts reaction
Friedel-Crafts α-(acyl)methylthiomethylations of aromatic compounds with α-ethoxycarbonyl, -acetyl, -benzoyl, and -cyano-α-(methylthio)methyl chlorides are described. The resulted products are easily converted to acylmethylated aromatics such as phenylacetate and phenylacetone by reductive desulfurization.
Tamura,Shindo,Uenishi,Ishibashi
p. 2547 - 2548
(2007/10/02)
A New Use of the Tetrahydrofuran/Powdered Potassium Hydroxide System: Convenient α-Sulfenylation of Ketones and Preparation of Dialkyl Polysulfides
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Morel, Georges,Marchand, Evelyne,Foucaud, Andre
p. 918 - 921
(2007/10/02)
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