O-Vinyldiaryl- and O-vinylaryl(hetaryl)ketoximes: a breakthrough in O-vinyloxime chemistry

O-Vinyldiarylketoximes and O-vinylaryl(hetaryl)ketoximes, a novel family of stable O-vinyloximes, are synthesized by a straightforward, unusually fast vinylation of diarylketoximes and aryl(hetaryl)ketoximes with acetylene in a superbase system of KOH–DMSO (60–80°C, 5–7 min). Yields of up to 90% wer...

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Published inTetrahedron Vol. 58; no. 50; pp. 10043 - 10046
Main Authors Zaitsev, Alexey B, Vasil'tsov, Alexander M, Schmidt, Elena Yu, Mikhaleva, Al'bina I, Morozova, Ludmila V, Afonin, Andrey V, Ushakov, Igor' A, Trofimov, Boris A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.12.2002
Elsevier
Subjects
acetylene
Chemistry
Chemistry, Organic
ketones
oximes
Physical Sciences
Science & Technology
superbase system
vinylation
vinylation
ketones
oximes
acetylene
superbase system
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Summary:O-Vinyldiarylketoximes and O-vinylaryl(hetaryl)ketoximes, a novel family of stable O-vinyloximes, are synthesized by a straightforward, unusually fast vinylation of diarylketoximes and aryl(hetaryl)ketoximes with acetylene in a superbase system of KOH–DMSO (60–80°C, 5–7 min). Yields of up to 90% were obtained, thus introducing into organic synthesis a new group of highly promising building blocks and monomers. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01304-2