6-Oxocyclohexa-2,4-dienylideneketene: A Highly ...
|Title||6-Oxocyclohexa-2,4-dienylideneketene: A Highly Reactive ?-Oxoketene|
|Author(s)||R. Liu, J. Lusztyk, M. McAllister, T. Tidwell, B. Wagner|
|Journal||Journal of the American Chemical Society|
|Abstract||Abstract: The title ketene 2 has been generated by laser flash photolysis and observed in solution for the first time, using time-resolved infrared spectroscopy. The kinetics of the reactivity of 2 with H2O, MeOH, and Et2NH with relative reactivities of 1.0, 2.0, and 73 have been measured. These are the first direct measurements of the reactivities of a ketene with these different nucleophiles under the same conditions. Ab initio molecular orbital calculations indicate the hydration occurs by in-plane attack of the H2O molecule on the ketenyl carbonyl through a pseudopericyclic transition state with assistance by coordination to the keto-carbonyl.|
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