Oxidative Coupling Of Phenols Research Articles

The phenoxylium ion from α-tocopherol spirodimer and its significance for the mechanism of oxidative coupling in phenols

The characteristic n.m.r. behaviour shown by the spirodimer (IIIa) from α-tocopherol, and its behaviour in ascorbic acid reductions, shows a dependence upon acid catalysis explicable in terms of a phenoxylium ion (X) and designates one area in which oxidative coupling of phenols would have ionic rather than radical mechanisms.

Studies on the syntheses of heterocyclic compounds. Part CCCXCIII. Synthesis of norerythrinadienone by phenolic oxidative coupling

Oxidation of N-(3-hydroxy-4-methoxybenzyl)-3-hydroxy-4-methoxyphenethylamine (6) with potassium ferricyande gave norerythrinadienone (3), which was converted into 6-acetyl-5,6,7,8-tetrahydro-2,3,10,11-tetramethoxydibenz[c,e]azocine (15). N-Acetyl-N-(3-hydroxy-4-methoxybenzyl)-4-hydroxy-3-methoxyphenethylamine (19) was oxidised to afford the corresponding dienone (20), which was transformed into compound (15)via the triacetate (21).

The biosynthesis of pilocereine. Part II

Pilocereine is shown to be formed directly, by phenolic oxidative coupling, from lophocerine.

Studies on the syntheses of heterocyclic compounds. Part CDXXXII. Synthesis of (±)-thalicsimidine by a possible biosynthetic route

Phenolic oxidative coupling of the diphenolic benzylisoquinolines (21) and (22) with potassium ferricyanide afforded the aporphine (3) and the spirocyclohexadienones (23a and b), respectively. The dienones (23a and b) were treated with acid to give two aporphines (4) and (5). Methylation of compounds (3) and (5) with diazomethane gave (±)-thalicsimidine (1).

Biosynthesis of cularine

Phenolic oxidative coupling of the diphenolic isoquinoline (I), followed by O-methylation, gave cularine (V) and concentrine type compound (VII) while the same reaction of the isoquinoline (II) gave the dienones (IXa) and (IXb).

Studies on the syntheses of heterocyclic compounds. Part CCCLXXXII. Phenolic oxidative coupling of reticuline by use of various reagents

The phenolic oxidative coupling of reticuline (III) to give pallidine (IV) and isoboldine (V), with the reagents potassium ferricyanide, vanadyl trichloride, and silver carbonate, has been examined. The reactions of p-cresol with silver carbonate and with silver nitrate are also described.

Studies on the syntheses of heterocyclic compounds. Part CDXLIII. An alternative synthesis of (±)-glaziovine by photolysis and phenolic oxidation

Photolysis of 8-bromo-1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxybenzyl)-6-methoxy-2-methylisoquinoline (12) afforded (±)-glaziovine (1). Phenolic oxidative coupling of compound (12) also gave the alkaloid (1).

Syntheses of a proerythrinadienone by phenolic oxidation and a morphinandienone system by a photo-pschorr reaction

Phenolic oxidative coupling of ethyl 1,2,3,4-tetrahydro-6-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-7-methoxyisoquinoline-2-carboxylate (2c) with potassium ferricyanide afforded the indenoisoquinoline (3c), which rearranged on treatment with acid. Spectral data, and methylation of the rearrangement product and comparison with the dienone (22) obtained from the diazotisation of the aminobenzylisoquinoline (15), followed by photolysis, excluded the morphinan structure (12), and confirmed the dibenz[d,f]indole structure (13).

Block Copolymers by Oxidative Coupling of Phenols

Block Copolymers by Oxidative Coupling of Phenols

The directing effect of annelated rings in aromatic systems—II: Synthesis and oxidation of 2,3-dihydro-5-benzo-furanols-I. An apparent mills-nixon effect in oxidative coupling of phenols

2,3Dihydro-5-benzofuranols related to β- and γ-tocopherol and to tocol have been synthesized and their oxidation with alkaline ferricyanide has been studied. Oxidation of 2,3-dihydro-2,2-dimethyl-5-benzofuranol gave a spiroketal trimer 10 by CC and CO coupling via the 6-position of the molecule. This indicates a directing effect on the oxidative coupling by the annelated 5-membered heterocyclic ring which is in accord with the predictions based on the Mills-Nixon effect. Similar oxidation of 2,3-dihydro-2,2,4,7-tetramethyl-5-benzofuranol and of 2,3-dihydro-2,2,6,7-tetramethyl-5-benzofuranol (analogues of β- and γ-tocopherol, respectively) gave the hydroxyquinones 11 and 12 by reactions involving opening of the heterocyclic ring.

A novel formation of the indole derivatives by phenolic oxidative coupling

A novel formation of the indole derivatives by phenolic oxidative coupling

Synthesis of 1-Benzyloxindole Derivatives for the Study of Phenolic Oxidative Coupling (Studies on the Syntheses of Heterocyclic Compounds. CCCXLVII)

At first the synthetic method of 6-hydroxy-1-(3-hydroxy-2-methoxybenzyl)-5-methoxy-2-oxindole (IIIa) was investigated as a precursor for Amaryllidaceae alkaloids. Secondly phenolic oxidative coupling of IIIa with ferric chloride or potassium ferricyanide under a variety of conditions, but failed.

Oxidative coupling of apigenin

Two novel biflavonyls have been prepared by phenolic oxidative coupling of apigenin, using alkaline potassium ferricyanide as the oxidizing agent. The structures of these dimers have been established as 3,3- and 3,3′-biapigeninyl respectively, primarily by spectroscopic methods. The synthetic compounds differ from all known natural biflavonyls in that linkage through the A ring of at least one of the flavonoid moieties is not observed. This indicates that the bioxynthesis of the natural compounds probably does not involve direct radical coupling.

Studies on the syntheses of heterocyclic compounds. Part CCCXIII. Phenolic oxidative coupling of a dihydroxy-1-phenethyl-1,2,3,4-tetra-hydroisoquinoline

The phenolic oxidative coupling of 1,2,3,4-tetrahydro-6-hydroxy-1-(3-hydroxy-2,4-dimethoxyphenethyl)-7-methoxy-2-methylisoquinoline (XV) with potassium ferricyanide gave abnormal products; phenylpropionaldehyde (XVI), dehydro-seco-homoerythrinadienone (XVII), seco-homoerythrinadienone (XVIII) and a quinoline derivative (XIX). Two synthetic routes to the starting diphenolic isoquinoline (XV) are described.

Synthesis of homoproaporphine by phenol oxidation (studies on the syntheses of heterocyclic compounds. CCCL)

Phenolic oxidative coupling of 1, 2, 3, 4-tetrahydro-1-(4-hydroxy-3-methoxyphenethyl)-6-methoxy-2-methyl-5-isoquinolinol (X) with ferric chloride afforded a cyclohexadienone (Ia) in 60% yield.

Syntheses of Aminoisoquinolines and Related Compounds. VIII. Total Synthesis of dl-Homolinearisine

8-Amino-1, 2, 3, 4-tetrahydro-7-methoxy-1-(4-methoxybenzyl)-2-methyl-6-isoquinolinol (IIa) was synthesized and the Pschorr reaction of this compound under alkaline conditions gave dl-homolinearisine, which could not be synthesized by the phenolic oxidative coupling method. Infrared and nuclear magnetic resonance spectra of the synthesized sample were superimposable with those of the natural product.

Oxidative coupling of phenols using vanadium tetrachloride and vanadium oxytrichloride

Oxidative coupling of phenols using vanadium tetrachloride and vanadium oxytrichloride

Selective Oxidative Coupling of Phenols by Silver Carbonate/Celite

Angewandte Chemie International Edition in EnglishVolume 8, Issue 6 p. 444-445 Communication Selective Oxidative Coupling of Phenols by Silver Carbonate/Celite Dr. V. Balogh, Dr. V. Balogh Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Search for more papers by this authorProf. Dr. M. Fetizon, Prof. Dr. M. Fetizon Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Search for more papers by this authorDr. M. Golfier, Corresponding Author Dr. M. Golfier Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Search for more papers by this author Dr. V. Balogh, Dr. V. Balogh Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Search for more papers by this authorProf. Dr. M. Fetizon, Prof. Dr. M. Fetizon Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Search for more papers by this authorDr. M. Golfier, Corresponding Author Dr. M. Golfier Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Université de Paris, Laboratoire de Stéréochimie, Faculté des Sciences, 91-Orsay (France)Search for more papers by this author First published: June 1969 https://doi.org/10.1002/anie.196904442Citations: 14AboutPDF 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 onFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume8, Issue6June 1969Pages 444-445 RelatedInformation

Intramolecular oxidative phenol coupling. A new method

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIntramolecular oxidative phenol coupling. A new methodMartin Alan Schwartz, Robert A. Holton, and Steven W. ScottCite this: J. Am. Chem. Soc. 1969, 91, 10, 2800Publication Date (Print):May 1, 1969Publication History Published online1 May 2002Published inissue 1 May 1969https://doi.org/10.1021/ja01038a073RIGHTS & PERMISSIONSArticle Views423Altmetric-Citations40LEARN 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 (159 KB) Get e-Alerts Get e-Alerts

Oxidative coupling of phenols. The biosynthesis of pilocereine.

The biosynthetic conversion, by oxidative phenolic coupling, of [N-methyl-14C]lophocerine into pilocereine has been observed in Lophocereus schottii. The devised pilocereine was labelled solely in the N-methyl groups. L-Methionine provides the N- and O-methyl groups of lophocerine.