Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 1, Pages 274-281Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b917793k
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Funding
- National Basic Research Program of China [2009CB825300]
- National Natural Sciences Foundation of China [20972135]
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Different from the reaction of 2,3-allenoic acids with Selectfluor (TM), 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor (TM) under different conditions in moderate yields. The reaction of 2,4,4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)-furanones were prepared. Based on the isolation and characterization of the minor. uorohydroxylation product E-5m, a mechanism has been proposed.
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