Abstract
It is known that ketone oximes react with acetylene in the superbasic system KOH–DMSO to give O-vinyloximes which readily undergo rearrangement into pyrroles (Trofimov reaction [1–3]). However, vinylation of 5-phenyl-1-vinyl-1H-pyrrole-2-carbaldehyde oxime (I) under analogous conditions gave exclusively 5-phenyl-1-vinyl-1H-pyrrole-2-carbonitrile (III, yield 67%) instead of expected O-vinyloxime II. It could be presumed that compound III was formed via dehydration of initial oxime I. Dehydration of aldehyde oximes to the corresponding nitriles in the system KOH–DMSO was described in [4]. However, oxime I almost did not undergo dehydration in the absence of acetylene (the yield of nitrile III did not exceed 4%). Therefore, we concluded that 5-phenyl-1vinyl-1H-pyrrol-2-carbonitrile (III) is formed as a result of elimination of vinyl alcohol (acetaldehyde) from O-vinyloxime II.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
