Solvent interactions in the allylation of piperidine

The reaction between allylbromide and piperidine has been studied in different protic and aprotic solvents. The reaction is first order with respect to allylbromide] and piperidine]. A correlation analysis of the rate data with solvent properties shows that polarity (Y), polarizability (P), and electrophilicity (E) of the solvent simultaneously influence the rate of reaction. From the regression analysis, information regarding the relative solvation of the reactants and the activated complex is obtained and a solvation model is proposed. © 2009 Wiley Periodicals, Inc. Int J Chem Kinet 41: 421–425, 2009