HALOGENATED KETENES .8. DIHALOKETENE REACTIVITIES IN AN ACYLATION REACTION

A kinetic study was made of the acylation of 3-pentanol with butylethyl-, dibromo-, diethyl-, dichloro-, dimethyl-, and diphenylketenes. All reactions were first order in ketene and first order in alcohol. The reactivity of the ketenes increases in the order given. The acylation of 3-pentanol with diphenylketene occurred at a faster rate in a nonpolar solvent. These results are interpreted to suggest a one-step process involving a cyclic transition state and establishes that the dihaloketenes are less reactive than diphenylketene with about the same activity as the dialkylketenes in the acylation of 3-pentanol. © 1969, American Chemical Society. All rights reserved.