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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Bibliographic Details
Published in:Tetrahedron 2002-12, Vol.58 (50), p.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: Article
Language:English
Subjects:
acetylene
ketones
oximes
superbase system
vinylation
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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