Liu, R. C. -Y, et al. “6-Oxocyclohexa-2,4-Dienylideneketene: A Highly Reactive α-Oxoketene”. Journal of the American Chemical Society, vol. 120, no. 25, 1998, pp. 6247-51, https://doi.org/10.1021/ja980060t.

Genre

  • Journal Article
Contributors
Author: Liu, R. C. -Y
Author: Lusztyk, J.
Author: Tidwell, T. T.
Author: Wagner, Brian D.
Author: McAllister, M. A.
Date Issued
1998
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.

Note

Contribution from the Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada, Department of Chemistry, University of North Texas, Denton, Texas 76203, Steacie Institute for Molecular Sciences, National Research Council,(TRUNCATED)

Source type: Electronic(1)

Language

  • English
Page range
6247-6251
Host Title
Journal of the American Chemical Society
Host Abbreviated Title
J. Am. Chem. Soc.
Volume
120
Issue
25
ISSN
0002-7863
DOI
https://doi.org/10.1021/ja980060t

Department