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1995•Journal of the Chemical Society Chemical CommunicationsRequires access

New trialkylsilyl enol ether chemistry: direct 1,2-bis-azidonation of triisopropylsilyl enol ethers: an azido-radical addition process promoted by TEMPO

Philip Magnus, Michael B. Roe, Christopher Hulme

Open publisher page 56 citations

Abstract

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.

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What this paper is about

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.

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Available abstract

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.

Key concepts: Chemistry, Enol, Enol ether, Nucleophile, Acetylene, Ether, Medicinal chemistry, Organic chemistry

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New trialkylsilyl enol ether chemistry: direct 1,2-bis-azidonation of triisopropylsilyl enol ethers: an azido-radical addition process promoted by TEMPO — Research Paper | ScholarLens