Journal of Physical Organic Chemistry
oscillatory reaction, reaction mechanism, spectroscopy
NMR and GC/MS spectroscopy of the organic extracts of the oscillatory bromate-1,4-cyclohexanedione reaction illustrate the presence of ring-opening products 5-(dibromomethylene)-2(5H)-furanone, (E)-5,5,5-tribromo-4-oxo-2-pentenoic acid, and dibromoacetic acid, particularly at elevated temperatures. The loss of a carbon atom from the six-membered ring after ring opening led to gas formation and such a process became more vigorous at >60 °C, with the direct observation of bubbles in a stirred batch reactor. Gravimetric experiments confirm that the amount of carbon dioxide gas produced increases rapidly with reaction temperature. Parallel experiments suggest that the ring-opening process involves the oxidation of brominated benzoquinones by bromate. Copyright © 2010 John Wiley & Sons, Ltd.
Funding Reference Number
Feng, Jiamin; Green, James R.; Johnson, Samuel A.; and Wang, Jichang. (2011). CO2 Production in the Bromate-1,4-Cyclohexanedione Oscillatory Reaction. Journal of Physical Organic Chemistry, 24 (6), 507-512.