The Kinetics and Mechanism of the Reaction of Diphenyldiazomethane with 2,4-Dinitrophenol in Ethanol

Abstract

Diphenyldiazomethane reacts with 2,4-dinitrophenol in ethanol to give a mixture of benzhydryl ethyl ether and benzhydryl 2,4-dinitrophenyl ether. The phenolic ether appears to result from a direct reaction of diphenyldiazornethane with 2,4-dinitrophenol while the benzhydryl ethyl ether is formed in a stepwise reaction initiated by undissociated 2,4-dinitrophenol or ethyloxonium ion acting as general-acid catalysts. The effects of inert salt, water and lithium 2,4-dinitrophenoxide on the reaction rate have been determined and correlated with the proposed reaction mechanisms.

Additional details