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Treatment of triisopropylsilyl enol ethers with PhIO/TMSN3/TEMPO (cat.)–45 °C results in 1,2-bis-azidonation, which appears to occur through a radical addition process; the 1-azido group can be replaced by carbon nucleophiles such as allyl, methyl, cyano, acetylene and acetonyl.
P. Magnus, M. B. Roe and C. Hulme, J. Chem. Soc., Chem. Commun., 1995, 263 DOI: 10.1039/C39950000263
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