Kinetic Study of the Pyrolysis of 1- and 2-Phenylethyl Phenyl <i>N</i>-Tosylsulfilimines

Abstract

Abstract The pyrolysis of 1-phenylethyl phenyl N-tosylsulfilimine was found to proceed more than 103 times faster than that of ethyl phenyl derivative. The large rate enhancement suggests that the mechanism changes from an ideal cis-elimination to nearly El type. However, substituent effect, kinetic isotope effect with 1-phenylethyl-2,2,2-d3 phenyl N-tosylsulfilimine and solvent effect clearly reveal that the reaction proceeds via an intramolecular concerted process.