Iminoxyl radicalsvs. tert-butylperoxyl radical in competitive oxidative C–O coupling with β-dicarbonyl compounds. Oxime ether formation prevails over Kharasch peroxidation Full article
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RSC Advances
ISSN: 2046-2069 |
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| Output data | Year: 2018, Volume: 8, Number: 11, Pages: 5670-5677 Pages count : 8 DOI: 10.1039/c7ra13587d | ||
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Abstract:
Oxidative coupling of oxime and β-dicarbonyl compounds dominates in a β-dicarbonyl compound/oxime/Cu(II)/t-BuOOH system; in the absence of oxime, oxidative coupling of t-BuOOH and a β-dicarbonyl compound (Kharasch peroxidation) takes place. The proposed conditions for oxidative coupling of oximes with dicarbonyl compounds require only catalytic amounts of copper salt and t-BuOOH serves as a terminal oxidant. The C–O coupling reaction proceeds via the formation of tert-butoxyl, tert-butylperoxyl and iminoxyl radicals. Apparently, tert-butylperoxyl radicals oxidize oxime into iminoxyl radical faster than they react with β-dicarbonyl compounds forming the Kharasch peroxidation product. Iminoxyl radicals are responsible for the formation of the target C–O coupling products; the yields are up to 77%.
Cite:
Krylov I.B.
, Paveliev S.A.
, Shumakova N.S.
, Syroeshkin M.A.
, Shelimov B.N.
, Nikishin G.I.
, Terent'ev A.O.
Iminoxyl radicalsvs. tert-butylperoxyl radical in competitive oxidative C–O coupling with β-dicarbonyl compounds. Oxime ether formation prevails over Kharasch peroxidation
RSC Advances. 2018. V.8. N11. P.5670-5677. DOI: 10.1039/c7ra13587d WOS Scopus OpenAlex
Iminoxyl radicalsvs. tert-butylperoxyl radical in competitive oxidative C–O coupling with β-dicarbonyl compounds. Oxime ether formation prevails over Kharasch peroxidation
RSC Advances. 2018. V.8. N11. P.5670-5677. DOI: 10.1039/c7ra13587d WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000424465500004 |
| Scopus: | 2-s2.0-85041747051 |
| OpenAlex: | W2786549023 |