Journal
TETRAHEDRON
Volume 67, Issue 43, Pages 8353-8359Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.08.058
Keywords
Polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine; Microwave; Epoxide; Pyridine N-oxide; Spiro fused 5-imidazolone
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Funding
- National University of Singapore [R-143-000-399-112]
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A thermally stable polymer-supported oxidant has been developed. Polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine was applied to microwave-assisted reactions that occurred at high temperatures and was shown to oxidize alkenes, silyl enol ethers, and pyridines to the corresponding epoxides and pyridine N-oxides in excellent to good yields and with much shorter reaction times. It also enabled tetrahydrobenzimidazoles to be oxidatively rearranged to Spiro fused 5-imidazolones in a more efficient manner. Recycling of the polymer-supported oxidant is also possible with minimal loss of activity after several reoxidations. (C) 2011 Elsevier Ltd. All rights reserved.
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