Generation of 6-methylene-2,4-cyclohexadienylidene ketene by flash photolysis of benzocyclobutenone in aqueous solution and study of the reactions of this ketene in that medium
2003
Flash photolysis of benzocyclobutenone in aqueous solution produced a transient species with a microsecond lifetime whose rates of decay were measured in perchloric acid, sodium hydroxide, and buffer solutions over the acidity range [H+] 1 × 1013 100 M. This produced a rate profile, isotope effects, and buffer behaviour typical of ketene reactions, and that, together with product identification, served to identify this transient as 6-methylene-2,4-cyclohexadienylidene ketene, formed by electrocyclic opening of the four-membered ring of benzocyclobutenone. Comparison of rates of reaction of this ketene with those of its saturated analog, pentamethyleneketene, produced some expected as well as some unexpected results. Key words: cyclobutenone chemistry, electrocyclic ring opening, ketene hydration, rate profile, solvent isotope effects.
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