Journal of the American Chemical Society

Halomethyl-metal compounds. LXIII. Insertion of phenyl (bromodichloromethyl) mercury-derived dichlorocarbene into benzylic carbon-hydrogen bonds. …

D Seyferth, YM Cheng

Index: Seyferth,D.; Cheng,Y.M. Journal of the American Chemical Society, 1973 , vol. 95, p. 6763 - 6770

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Citation Number: 22

Abstract

Abstract: The insertion of phenyl (bromodichloromethy1) mercury-derived dichlorocarbene into the benzylic CH bond of (+)-Zphenylbutane occurs with predominant retention of configuration. The kinetic deuterium isotope effect for this process was determined to be 2.5. In a Hammett study, pairs of substituted cumenes, ZC6H4-CMezH (Z= p-CHa, H, pF, p-C1, m- CFs), were allowed to compete for a deficiency of PhHgCC1, Br. These ex-periments ...

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