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- Title
Oxidative Cleavage of β-Keto Sulfones via Nitrous Acid.
- Authors
Abdel-Aziz, Hatem A.
- Abstract
The reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones 3a-e afforded the unexpected arenecarboxylic acids 12a-e, formic acid 14, and benzene/4-toluenesulfinic acid 15a, b through oxidative cleavage reaction. 4-Chlorobenzoic acid (12a), [1,1'-biphenyl]-4-carboxylic acid (12b), 2-naphthoic acid (12c), 2-thiophenecarboxylic acid (12d), and 2-benzofurancarboxylic acid (12e) were isolated in 72%, 62%, 55%, 58%, and 62% yields, respectively. The reported mechanistic pathways proposed the production of 1-aryl-2-(phenyl/tolylsulfonyl)ethane-1,2-dione 7 instead of arenecarboxylic acids 12. A mechanistic pathway to explain the reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones 3a-e was suggested. In this pathway, the intermediate 1,2-oxazete 10 lost benzene/4-toluenesulfinic acid 15 to produce 1,2-oxazet-3-one 11. Ring cleavage of the latter intermediate afforded the arenecarboxylic acids 12.
- Subjects
BENZENE; SULFONES; ORGANOSULFUR compounds; NONCARBOXYLIC acids; NITROGEN compounds
- Publication
Journal of Chemistry, 2014, p1
- ISSN
2090-9063
- Publication type
Article
- DOI
10.1155/2014/524930