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Cover Picture: The Multiple Reactions in the Monochlorodimedone Assay: Discovery of Unique Dehalolactonizations under Mild Conditions (Asian J. Org. Chem. 10/2015)
Author(s) -
China Hideyasu,
Okada Yutaka,
Dohi Toshifumi
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500315
Subject(s) - chemistry , aqueous solution , acetic acid , halogenation , decomposition , cover (algebra) , chromatography , reaction mechanism , combinatorial chemistry , organic chemistry , catalysis , mechanical engineering , engineering
The monochlorodimedone assay is an easy spectrophotometry method for halogenation in aqueous solution; however, unexpected spontaneous decomposition of the assumed product has been hiding in the assay. Detection of lactone products indicated that a significant aqueous reaction occurs during the decomposition. A unique delaholactonization of haloketo acids was discovered when a common separation operation using NaHCO 3 solution was performed with the intention of removing the acetic acid of the buffer component in the crude extract. It was also clarified that the reaction mechanism of the dehalolactonization goes via a cyclopropanone intermediate in water. More information can be found in the Full Paper on page 1065 by H. China et al. (DOI: 10.1002/ajoc.201500210).