6-oxocyclohexa-2,4-dienylideneketene

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Title 6-oxocyclohexa-2,4-dienylideneketene: a highly reactive α-oxoketene
Author(s) R. C. -Y Liu, J. Lusztyk, M. A. McAllister, T. T. Tidwell, Brian D. Wagner
Journal Journal of the American Chemical Society
Date 1998
Volume 120
Issue 25
Start page 6247
End page 6251
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.
DOI 10.1021/ja980060t

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