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

doi:10.1039/C39950000263

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

Research output: Contribution to journal › Article › peer-review

60 Scopus 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.

Original language	English (US)
Pages (from-to)	263-265
Number of pages	3
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	2
DOIs	https://doi.org/10.1039/C39950000263
State	Published - 1995
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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title = "New trialkylsilyl enol ether chemistry: Direct 1,2-bis-azidonation of triisopropylsilyl enol ethers: An azido-radical addition process promoted by TEMPO",

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.",

author = "Philip Magnus and Roe, \{Michael B.\} and Christopher Hulme",

year = "1995",

doi = "10.1039/C39950000263",

language = "English (US)",

pages = "263--265",

journal = "Journal of the Chemical Society D: Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "2",

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T2 - Direct 1,2-bis-azidonation of triisopropylsilyl enol ethers: An azido-radical addition process promoted by TEMPO

AU - Magnus, Philip

AU - Roe, Michael B.

AU - Hulme, Christopher

PY - 1995

Y1 - 1995

N2 - 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.

AB - 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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UR - https://www.scopus.com/pages/publications/37049090118#tab=citedBy

U2 - 10.1039/C39950000263

DO - 10.1039/C39950000263

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ER -

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

Abstract

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