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CO 2 production in the bromate‐1,4‐cyclohexanedione oscillatory reaction
Author(s) -
Feng Jiamin,
Green James R.,
Johnson Samuel A,
Wang Jichang
Publication year - 2011
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1795
Subject(s) - chemistry , bromate , ring (chemistry) , gravimetric analysis , spectroscopy , carbon dioxide , photochemistry , medicinal chemistry , organic chemistry , ion , physics , quantum mechanics
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.