Aryl Ketoximes Research Articles

Pyrroles from ketoximes and acetylene

Some of the typical experiments are given in Table 1 to illustrate the obtained results. It follows from the data in Table 1 that the final result of the reaction depends largely on the structure of the ketoxime and on the reaction conditions. Thus, N-vinyl-2-(4-phenylphenyl)pyrrole (IIIa) was mainly formed with a yield of 68 % from 4-phenylacetophenone oxime (Ia) with acetylene under pressure in the presence of potassium hydroxide at 100~ while the pyrrole (IIa) was obtained with a yield of 16% under these conditions (expt. 2). With lithium hydroxide, which usually catalyzes the construction of the pyrrole ring sufficiently actively in the reaction of alkyl aryl ketoximes with acetylene and is almost inactive in the vinylation of the intermediately formed pyrroles [8,9], it is possible to synthesize the pyrrole (IIa) free from its N-vinyl derivative with a higher yield (42%, expt. 1). On account of the reduced catalytic activity of lithium hydroxide compared with potassium hydroxide [9] the vinylation rate of the ketoxime (Ia) and the rearrangement rate of the intermediate (O-vinyl-4-phenylacetophenone oxime) to the pyrrole (IIa) are reduced, and the conversion of the ketoxime (Ia) in the same time is consequently reduced from 100 to 67%. In addition, the reaction is accompanied by regeneration of the 4-phenylacetophenone (yield 10%).

ChemInform Abstract: Pyrroles from Ketoximes and Acetylene. Part 44. Methyl Aryl Ketoximes with Reactive Substituents.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Pyrroles from ketoximes and acetylene. 44. Methyl aryl ketoximes with reactive substituents

The Trofimov reaction was extended to methyl aryl ketoximes with substituents in the benzene ring that are unstable with respect to the action of a strongly basic medium. The corresponding pyrroles and their 1-vinyl derivatives were obtained. 4-Nitroacetophenone oxime, from which only 2-phenyl- and 1-vinyl-2-phenylpyrrole were obtained, and 4-bromoacetophenone oxime, the reaction of which leads to the formation of 1-vinyl-2-(4-vinyloxyphenyl)pyrrole in addition to the principal 2-(4-bromophenyl)pyrrole, constituted exceptions.

ChemInform Abstract: O‐Aryl Ketoximes. Part 1. O‐Arylation of Ketoximes with Nitrochlorobenzenes.

AbstractThe O‐arylation of the aryl ketoximes (I) with 2‐ or 4‐nitrochlorobenzene (II) is performed in a DMSO/THF solution at moderate temperature.

Synthesis of substituted methyl aryl ketone pyrimidinyloximes and their reactions with nucleophiles

Chloropyrimidines react readily with the sodium salts of alkyl aryl ketoximes to give acetophenone O-(2,4-dimethylpyrimidin-6-yl)- and O-(4,6-dimethylpyrimidin-2-yl)oximes, the oximino-groups in which readily undergo nucleophilic substitution.

ChemInform Abstract: Pyrroles from Ketoximes and Acetylene. Part 37. Application of Vinyl Chloride Instead of Acetylene for the Synthesis of Arylpyrroles from Ethyl Aryl Ketoximes.

ChemInformVolume 20, Issue 12 Heterocyclic Compounds ChemInform Abstract: Pyrroles from Ketoximes and Acetylene. Part 37. Application of Vinyl Chloride Instead of Acetylene for the Synthesis of Arylpyrroles from Ethyl Aryl Ketoximes. I. A. ALIEV, I. A. ALIEV Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorS. N. ZEINALOVA, S. N. ZEINALOVA Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorB. R. GASANOV, B. R. GASANOV Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorA. I. MIKHALEVA, A. I. MIKHALEVA Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorS. E. KOROSTOVA, S. E. KOROSTOVA Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this author I. A. ALIEV, I. A. ALIEV Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorS. N. ZEINALOVA, S. N. ZEINALOVA Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorB. R. GASANOV, B. R. GASANOV Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorA. I. MIKHALEVA, A. I. MIKHALEVA Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this authorS. E. KOROSTOVA, S. E. KOROSTOVA Irkutskii inst. org. khim. Sib. otd. Akad. nauk SSSRSearch for more papers by this author First published: March 21, 1989 https://doi.org/10.1002/chin.198912176Citations: 1Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article.Citing Literature Volume20, Issue12March 21, 1989 RelatedInformation

ChemInform Abstract: Asymmetric Catalysis. Part 29. Optically Active Primary Amines by Enantioselective Catalytic Hydrosilylation of Ketoximes.

AbstractAlkyl aryl ketoximes (I) [E/ Z Vmixtures of (I) are used as formed in the syntheses] undergo catalytic hydrosilylation with diphenylsilane (II) to give the silylamines (III) and (IV), which on hydrolysis yield the prim. amines (V) and (VI).

ChemInform Abstract: CONVERSION OF O‐VINYL ALKYL ARYL(HETARYL) KETOXIMES TO PYRROLES IN THE POTASSIUM HYDROXIDE‐DMSO SYSTEM

Chemischer InformationsdienstVolume 14, Issue 28 Heterocyclic Compounds ChemInform Abstract: CONVERSION OF O-VINYL ALKYL ARYL(HETARYL) KETOXIMES TO PYRROLES IN THE POTASSIUM HYDROXIDE-DMSO SYSTEM B. A. TROFIMOV, B. A. TROFIMOVSearch for more papers by this authorS. E. KOROSTOVA, S. E. KOROSTOVASearch for more papers by this authorA. I. MIKHALEVA, A. I. MIKHALEVASearch for more papers by this authorL. N. SOBENINA, L. N. SOBENINASearch for more papers by this authorA. N. VASIL'EV, A. N. VASIL'EVSearch for more papers by this authorR. N. NESTERENKO, R. N. NESTERENKOSearch for more papers by this author B. A. TROFIMOV, B. A. TROFIMOVSearch for more papers by this authorS. E. KOROSTOVA, S. E. KOROSTOVASearch for more papers by this authorA. I. MIKHALEVA, A. I. MIKHALEVASearch for more papers by this authorL. N. SOBENINA, L. N. SOBENINASearch for more papers by this authorA. N. VASIL'EV, A. N. VASIL'EVSearch for more papers by this authorR. N. NESTERENKO, R. N. NESTERENKOSearch for more papers by this author First published: July 12, 1983 https://doi.org/10.1002/chin.198328180Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume14, Issue28July 12, 1983 RelatedInformation

Conversion of O-vinyl alkyl aryl (hetaryl) ketoximes to pyrroles in the KOH-DMSO system

Conversion of O-vinyl alkyl aryl (hetaryl) ketoximes to pyrroles in the KOH-DMSO system

Flash vacuum pyrolysis of aromatic oximes.

Flash vacuum pyrolysis (FVP) of benzaldoximes and aryl ketoximes afforded nitriles and additional aromatic compounds which were presumably generated from intermediary iminyl radicals. The FVP also gave benzoxazoles, which were presumably formed from iminoxyl radicals. Benzyl ketoximes afforded indoles together with fragmentation products of the iminyl radicals.

ChemInform Abstract: PYROLYSIS OF BENZOPHENONE OXIME CARBONATES‐ A POTENTIAL ROUTE TO ARYL IMINO ETHERS (ARYL IMIDATES)

AbstractAus den Ketoximen (I) und Phenylchlorformiat werden die Oximcarbonate (II) dargestellt, die bei 180‐200°C in die entsprechenden Imidate (III) übergehen.

Pyrolysis of benzophenone oxime carbonates: a potential route to aryl imino ethers (aryl imidates)

Aryl ketoxime carbonates have been found to undergo decompositions at temperatures ranging from 180–200°C to give carbon dioxide and aryl imino ethers (imidates). This pyrolysis could prove to be a general method for preparing aryl imino ethers. Formation of different imidates from the two geometric isomers (E- and Z-forms) of the ketoxime carbonates supports a mechanism involving the migration of the aryl group trans to the carbonate grouping. This is similar to that observed in the Beckmann rearrangement of ketoximes.

Synthesis and structure determination of a thermally labile anti-alkyl aryl ketoxime

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and structure determination of a thermally labile anti-alkyl aryl ketoximeJerry H. Smith, J. H. Heidema, E. T. Kaiser, Joseph B. Wetherington, and J. William MoncriefCite this: J. Am. Chem. Soc. 1972, 94, 26, 9274–9276Publication Date (Print):December 1, 1972Publication History Published online1 May 2002Published inissue 1 December 1972https://doi.org/10.1021/ja00781a074RIGHTS & PERMISSIONSArticle Views158Altmetric-Citations18LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (404 KB) Get e-Alerts Get e-Alerts

Preparation of oxazine derivatives and 2,4-diarylpyrroles from methyl aryl ketoximes

Some methyl aryl ketoximes have been shown to condense in the presence of EtMgBr to give 3,5-diaryloxazine derivatives. These in turn rearrange in conc hydriodic acid, with the formation of 2,4-diarylpyrroles in reasonable yields. Possible mechanisms for these reactions are discussed.