Abstract
The primayy step of the o-nitrobenzaldehyde-o-nitrosobenzoic acid photorearrangement in solution has been studied by flash absorption with 35 ps 355 nm light pulses. Flash photolysis of o-nitrobenzaldehyde in acetonitrile or THF solutions produces a transient absorption with a maximum at ca. 440 nm. Formation of the transient was < 35 ps, the laser pulse width, and within experimental error, no furthrr buildup was observed. The transient which decayed at nanosccond times is attributed to a remarkably reactive ketene intermediate formed by H abstraction of the aldehydic hydrogen by the excited state of the nitro group. Decay of the ketene was more rapid in water-acetonitrile, methanol-acetonitrile, tert-butyl alcohol and in THF than in acetonitrile solution. It is suggested that the intramolecular reaction of the ketene intermediate is enhanced in THF relative to acetonitrile because of the ability of THF to faciliaate proton transfer associated with the reaction.
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