Document Type

Article

Publication Date

6-11-2011

Publication Title

Journal of Physical Organic Chemistry

Volume

24

Issue

6

First Page

507

Last Page

512

DOI

10.1002/poc.1795

Keywords

oscillatory reaction, reaction mechanism, spectroscopy

Abstract

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

NSERC

Comments

This is the peer reviewed version of the following article: Feng, J.; Green, J.; Johnson, S.; Wang, J. (2011) “CO2 Production in the Bromate-1,4-Cyclohexanedione Oscillatory Reaction”, J. Phys. Org. Chem., 24, 507-512., DOI: 10.1002/poc.1795., which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/poc.1795/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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