The ultrasonically induced reaction of benzoyl chloride with nitrobenzene: an unexpected sonochemical effect and a possible mechanism.
A mixture of benzoyl chloride and nitrobenzene is not known to be chemically reactive, indeed the mixture is chemically inert when subjected individually to either ultrasonic irradiation or heating. However, if this system is initially subjected to ultrasound and then heated for several hours at 200 degrees C, a reaction does occur and the products are benzoic anhydride, hydrochloric acid, nitrous and nitric acid together with some minor products. To the best of our knowledge, this is the first example of a reaction where the effect of ultrasound does not appear to be the consequence of the direct action of acoustic cavitation bubbles. A possible explanation of this behaviour is advanced which involves an electron transfer reaction in which nitrobenzene is first activated by ultrasound and then acts as oxidant in the thermal stage of reaction.
Vinatoru
M
M
Romanian Academy, Costin D. Nenitzescu Institute of Organic Chemistry, 71141 Bucharest, P.O. Box 15-254, Romania. mvinator@cco.ro
Stavrescu
R
R
Milcoveanu
A B
AB
Toma
M
M
Mason
T J
TJ