Selective Mono-C-methylations of Arylacetonitriles and Arylacetates with Dimethylcarbonate: A Mechanistic Investigation

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Selective mono-C-methylations of arylacetonitriles and arylacetates with dimethylcarbonate: a mechanistic investigation.

The very high mono-C-methylation selectivity (>99%) of arylacetic acid derivatives (ArCH2X; X = CN, CO2Me) with dimethyl carbonate (DMC) is due to a mechanism that involves consecutive methoxycarbonylation, methylation, and demethoxycarbonylation steps. Important aspects of this mechanism are clarified herein by a kinetic investigation. In the case of arylacetonitriles, at 140 degrees C, the co...

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ژورنال

عنوان ژورنال: The Journal of Organic Chemistry

سال: 2002

ISSN: 0022-3263,1520-6904

DOI: 10.1021/jo0057699