Journal of The Chemical Society C: Organic最新文献

{"title":"Triterpenoid constituents of Lycopodium phlegmaria L","authors":"Y. Inubushi, T. Hibino, T. Harayama, T. Hasegawa, R. Somanathan","doi":"10.1039/J39710003109","DOIUrl":"https://doi.org/10.1039/J39710003109","url":null,"abstract":"From Lycopodium phlegmaria L. collected in Ceylon, eleven triterpenes, all of which belong to the serratenediol family, have been isolated. Serratenediol (I), serratenediol 3-acetate (II), serratriol (III), hydroxyserratenone (IV), and tohogenol (V) are known compounds. Phlegmanols A (VII), B (VIII), C (IX), D (X), E (XII), and phlegmaric acid (XI) are new compounds.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"23 1","pages":"3109-3114"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84982366","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Polyhalogeno-aromatic compounds. Part XXI. A novel reagent system for the N-oxidation of weakly basic N-heteroaromatic compounds","authors":"G. Chivers, H. Suschitzky","doi":"10.1039/J39710002867","DOIUrl":"https://doi.org/10.1039/J39710002867","url":null,"abstract":"A mixture of concentrated sulphuric acid, an organic acid, and hydrogen peroxide converts many polyhalogenated-N-heteroaromatic compounds into their N-oxides in good yield. The scope and limitations as well as the mode of action of this reagent are discussed. The use of a mixture of hydrogen peroxide and polyphosphoric acid for N-oxidation of certain polyhalogeno-N-heteroaromatic compounds is also described. An example of nucleophilic substitution in the pentachloropyridinium ion is reported.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"76 1","pages":"2867-2871"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85966312","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Curvularin. Part VII. Some acylations of 3,5-dihydroxytoluene and its dimethyl ether","authors":"H. Munro, O. C. Musgrave, R. Templeton","doi":"10.1039/J39710000095","DOIUrl":"https://doi.org/10.1039/J39710000095","url":null,"abstract":"3,5-Dihydroxytoluene is acylated in the 2-position by octanoyl chloride in the presence of aluminium chloride. In polyphosphoric acid it reacts with 7-oxo-octanoic acid and with crotonic acid to give the corresponding 4-acyl derivative and 7-hydroxy-2,5-dimethylchroman-4-one respectively. Under the same conditions 3,5-dimethoxytoluene and crotonic acid give the dioxobenzodipyran (V). Tin(IV) chloride effects the acylation of 3,5-dimethoxytoluene by crotonoyl chloride in the 2-position and by benzoyl chloride in the 2- and 6-position.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"58 1","pages":"95-98"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76772051","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Quinazolines. Part XVIII. A second stereospecific cis-addition of the elements of nitromethane across a tetrasubstituted ethylenic double bond. A concerted mechanism for the reaction of nitroacetic acid with enamines","authors":"W. Armarego, Toshihiko Kobayashi","doi":"10.1039/J39710003222","DOIUrl":"https://doi.org/10.1039/J39710003222","url":null,"abstract":"The reaction of ethyl 3,4,5,6-tetrahydroanthranilate with nitroacetic acid gave, stereospecifically, ethyl cis-2-amino-trans-2-nitromethylcyclohexanecarboxylate (7) in 70% yield. The stereochemistry was deduced by the following sequence of reactions: (7)→ ethyl cis-2-amino-trans-2-aminomethylcyclohexanecarboxylate (8)→ 3a-amino-trans-perhydroisoindol-1-one (9)→ 3a-(N′-phenylureido)-trans-perhydroisoindol-1-one (10)→ 8a-aminomethyl-3-phenyl-cis-perhydroquinazoline-2,4-dione hydrochloride (18)→ 8a-bromomethyl-3-phenyl-cis-perhydroquinazoline-2,4-dione (19)→ 8a-methyl-3-phenyl-cis-perhydroquinazoline-2,4-dione (20), in which the configuration at the asymmetric centres was preserved. Compound (20) was prepared from authentic methyl trans-2-methyl-cis-2-(N′-phenylureido)cyclohexanecarboxylate (22) by cyclisation with methanolic sodium hydroxide. Although this cyclisation in a deuteriated medium proceeded with complete exchange of the 4a-proton in the dione (20), it was shown to occur with retention of configuration by reduction with sodium dihydrobis-(2-methoxyethoxy)aluminate to cis-2-anilinomethyl-1,N-dimethylcyclohexylamine (25) and then to 1,8a-dimethyl-3-phenyl-cis-perhydroquinazoline (26), whose 1H n.m.r. spectrum was unambiguous.The trans stereochemistry of the isoindolone (9) was confirmed by reduction to 3a-amino-trans-perhydroisoindole (14) whose 1H n.m.r. spectrum was similar to that of 3a-methylanalogue (15) but different from that of 3a-methyl-cis-perhydroisoindole (16).This second observation of a stereospecific cis-addition of the elements of nitromethane strongly supports a concerted mechanism for the reaction of nitroacetic acid with enamines. Further evidence is reported from experiments in [2H3]nitromethane which show that no deuterium was incorporated into the nitromethane adducts.N.m.r. spectra of various compounds are discussed in connection with the generality of application of the principle that the protons in the alicyclic six-membered rings of reduced six–five, six–six and six–seven membered fused ring systems give a narrow band envelope for cis ring fusion and a wide band envelope for trans ring fusion.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"51 1","pages":"3222-3229"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76914296","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"New synthesis of hexacene","authors":"M. Satchell, B. Stacey","doi":"10.1039/J39710000468","DOIUrl":"https://doi.org/10.1039/J39710000468","url":null,"abstract":"The reaction of 9,10-dihydroxyanthracene-1,4(2H,3H)-dione with naphthalene-2,3-dicarbaldehyde gives 5,16-dihydroxyhexacene-6,15-quinone (2) in high yield. This compound can be converted into dihydrohexacene, and hence into hexacene, more efficiently than can similar compounds used in earlier syntheses of the polyacene. The use of copper(II) oxide in the dehydrogenation of dihydrohexacene is reported.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"118 1","pages":"468-469"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76994535","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Studies on the syntheses of heterocyclic compounds. Part CCCXCII. An alternative total synthesis of petaline","authors":"T. Kametani, T. Kobari, K. Fukumoto*, M. Fujihara","doi":"10.1039/J39710001796","DOIUrl":"https://doi.org/10.1039/J39710001796","url":null,"abstract":"Petaline (1) was synthesised by methylation of 1,2,3,4-tetrahydro-8-hydroxy-7-methoxy-1-(4-methoxybenzyl)-2-methylisoquinoline (12) prepared from 5-benzyloxy-2-bromo-4-methoxyphenethylamine (5) by two methods. Moreover, tetrahydroisoquinoline (12) was synthesised by Stevens reaction of 8-benzyloxy-1,2,3,4-tetrahydro-7-methoxy-2-(4-methoxybenzyl)isoquinoline methochloride (21).","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"295 1","pages":"1796-1800"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77180887","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Condensed thiophen ring systems. Part VI. Synthesis and some reactions of 5-methyl- and 5-chloro-3-benzo[b]thienyl-lithium","authors":"R. Dickinson, B. Iddon","doi":"10.1039/J39710002504","DOIUrl":"https://doi.org/10.1039/J39710002504","url":null,"abstract":"3-Bromo-5-methyl- and 3-bromo-5-chloro-2-benzo[b]thienyl-lithium were prepared and treated (i) with carbon dioxide, to give the corresponding 2-carboxylic acid, and (ii) with acid, to give the 3-bromo-derivatives of 5-methyl-and 5-chloro-benzo[b]thiophen, respectively. With n-butyl-lithium in ether at –70°C the 3-bromo-derivatives gave 5-methyl- and 5-chloro-3-benzo[b]thienyl-lithium, which reacted with carbon dioxide, NN-dimethylformamide, and dimethyl sulphate to give the corresponding 3-carboxylic acid, 3-carbaldehyde, and 3-methyl derivative, respectively. 3,5-Dimethylbenzo[b]thiophen was also prepared by Huang-Minlon reduction of 5-methylbenzo-[b]thiophen-3-carbaldehyde.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"13 1","pages":"2504-2506"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80905064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Photodimerisation of 2-benzyl-5-p-bromobenzylidenecyclopentanone, a crystal–crystal transformation: X-ray study of the dimer","authors":"D. Whiting","doi":"10.1039/J39710003396","DOIUrl":"https://doi.org/10.1039/J39710003396","url":null,"abstract":"2-Benzyl-5-p-bromobenzylidenecyclopentanone photodimerises in the crystalline state, yielding directly a crystalline dimer. The dimer crystallises in the orthorhombic space group Pbca with Z= 4 in a unit cell of dimensions: a= 10·27, b= 8·98, and c= 32·96 A. The X-ray crystal structure was solved from diffractometer data by the heavy-atom method with conventional Patterson and fourier techniques and refined by least-squares methods to R 0·134 for 1674 independent reflections.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"25 1","pages":"3396-3398"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80947306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Compounds related to 1-hydroxymethylindane-2-carboxylic acid","authors":"D. Peacock","doi":"10.1039/J39710003506","DOIUrl":"https://doi.org/10.1039/J39710003506","url":null,"abstract":"The preparation of the lactone of cis-1-hydroxymethylindane-2-carboxylic acid is described and of some substituted amino-derivatives of 1-methylindene-2-carboxylic acid. Some other reactions of ethyl γ-bromo-α-benzylaceto-acetate are described.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"18 1","pages":"3506-3510"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80985961","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Highly fluorinated heterocycles. Part V. The preparation and some reactions of tetrafluorothiophen and some polyfluorothiophens","authors":"J. Burdon, J. G. Campbell, I. W. Parsons, J. Tatlow","doi":"10.1039/J39710000352","DOIUrl":"https://doi.org/10.1039/J39710000352","url":null,"abstract":"Tetrafluorothiophen has been prepared by dehydrofluorination of 3H/4H-hexafluorothiolan by molten alkali. It did not react with bromine nor did it polymerise rapidly, unlike tetrafluorofuran. It reacted with sodium methoxide with displacement of the 2-fluorine, as was proved by an independent synthesis of the other possible isomer, 2,3,5-trifluoro-4-methoxythiophen. 2,5-Difluorothiophen and 2,5-difluoro-3-methoxythiophen have also been prepared. The methoxythiophens all polymerised rapidly. In the 19F n.m.r. spectra of the polyfluorothiophens, the α-fluorines resonate to high field of the β; also, the 2–5 F–F couplings are large (26–31 Hz).","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"37 1","pages":"352-355"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81126260","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}