Previous reports have shown that the solvent used in indium mediated allylations may have drastic effects on the rates of reaction, yields, regiochemistry, and stereochemical outcomes (including diastereo- and entioselectivity). We report kinetic measurements for the reaction of cinnamyl chloride on indium metal in ethanol/water mixes. We show that the reaction rate increases slightly as the percent water in ethanol increases from 0 to 20%. Perhaps more importantly we show that the induction time depends drastically on the percent water. Insights into the mechanism of indium mediated allylations based on these observations are discussed in the broader context of previously reported solvent effects. Plans for future measurement of Arrhenius parameters are described.

Solvent effects on the kinetics of indium mediated allylations

245th National Meeting (2013)

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