p-Methoxybenzoyl p-Nitrobenzoyl Peroxide Revisited: Catalysis by Silica

Article abstract of DOI:10.1021/jo00133a010

The decomposition of p-methoxybenzoyl p-nitrobenzoyl peroxide (1) in benzene/silica slurries at room temperature is faster than in benzene solution by 5 orders of magnitude.The first product of the reaction is entirely or mainly the carboxy inversion compound, p-methoxyphenyl p-nitrobenzoyl carbonate (2), which also decomposes on the silica.The products from experiments in which 2 is the initial reagent are the same as those from the peroxide.The most important are p-methoxyphenyl p-nitrobenzoate, p-methoxyphenol, and p-nitrobenzoic acid.The absence within the limits of GC/MS of anisic acid, p-methoxybiphenyl, p-nitrobiphenyl, p-nitrophenyl anisate, p-methoxy-p'-nitrobiphenyl, phenyl p-nitrobenzoate, phenyl anisate, and phenyl p-nitrobenzoate indicates that the decomposition of 1 under these conditions produces no free radicals.