Substituent Effects on Suspected Phenonium Ion Reactions

概要

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The stereochemistry of the various conversions in the 1,2-diphenyl-1-propyl system was measured as a function of aromatic substituent. For β-anisyl groups the reaction occurred with retention of configuration. For compounds with indifferent electron donating aryl groups, the conversions were stereoselective forming mostly threo product. For β-p-nitrophenyl groups the stereochemical course of the reaction was "racemization." The latter reactions were associated with the presence of open ions. In certain reactions, acetate products were formed in low yield with retention of configuration, irrespective of substituent. The kinetics of ethanolysis were consistent with (partial) bridged ion formation for the threo isomers and with extensive open ion formation for the erythro species.
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