ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT[5]ParacyclophaneLeonardus W. Jenneskens, Franciscus J. J. De Kanter, Paulus A. Kraakman, Lucas A. M. Turkenburg, Willem E. Koolhaas, Willem H. De Wolf, Friedrich Bickelhaupt, Yoshito Tobe, Kiyomi Kakiuchi, and Yoshinobu OdairaCite this: J. Am. Chem. Soc. 1985, 107, 12, 3716–3717Publication Date (Print):June 1, 1985Publication History Published online1 May 2002Published inissue 1 June 1985https://pubs.acs.org/doi/10.1021/ja00298a051https://doi.org/10.1021/ja00298a051research-articleACS PublicationsRequest reuse permissionsArticle Views489Altmetric-Citations95LEARN 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 InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
Abstract [6]paracyclophane (1) has been synthesized by oxidative decarboxylation of [6.2.2]propellenecarboxylic acid with lead tetraacetate. Vapor phase thermolysis of 1 affords 3-methylene-spiro[5.5]undeca-1,4-diene predominantly, while acid-catalyzed rearrangement of 1 gives the meta and ortho isomers in a ratio of 1:3.
Abstract The cyclization of amides derived from ethenetricarboxylic acid bearing tert ‐amino groups has been examined. The amides were efficiently converted to piperidine derivatives (2‐piperidones) upon heating in a polar solvent (e. g., DMSO or DMF) via intramolecular hydride transfer and subsequent ring closure. The reaction was less efficient in the presence of a Lewis acid. The reactivity varies depending on the alkyl substituents of tert ‐amino groups, probably due to steric effects. The hydride transfer/cyclization mechanism was investigated by DFT calculations. The reaction of the carboxylic acid and relatively bulky diamines such as diisopropyl‐substituted diamine in the presence of amide condensation reagents at 60 °C gave the piperidine derivatives in a one‐pot reaction. The reaction of the diisopropylamine substituted piperidine product with primary amines gave secondary amine‐substituted piperidines.
The rhodium(i)/chiral Ph-bpe-catalyzed reaction of vinylarenes with formaldehyde provides an accessible protocol for asymmetric hydroformylation to enantioenriched aldehydes in high yields.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of 8-(methoxycarbonyl)[6]paracyclophane-3,4-dioneYoshito Tobe, Takuya Furukawa, Kazuya Kobiro, Kiyomi Kakiuchi, and Yoshinobu OdairaCite this: J. Org. Chem. 1989, 54, 2, 488–491Publication Date (Print):January 1, 1989Publication History Published online1 May 2002Published inissue 1 January 1989https://doi.org/10.1021/jo00263a044Request reuse permissionsArticle Views101Altmetric-Citations6LEARN 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 (588 KB) Get e-Alertsclose Get e-Alerts
Zinc Lewis acid-catalyzed cyclization of ethenetricarboxylate derivatives 1 with 2-ethynylanilines has been examined. Reaction of 1,1-diethyl 2-tert-butyl ethenetricarboxylate 1b with 2-(trimethylsilylethynyl)aniline substrates in the presence of Zn(OTf)(2) gave bridged quinoline derivatives in 43-85% yield. The reaction of 1b with 2'-aminoacetophenone also gave the bridged quinoline derivative in 41% yield. Thermal reaction of bridged quinolines (180-190 degrees C) afforded indole derivatives in moderate to good yields.
This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPyrolysis of bicyclo[n.2.2] bridgehead acetates with a bridgehead double bondYoshito Tobe, Toshiro Kishimura, Kiyomi Kakiuchi, and Yoshinobu OdairaCite this: J. Org. Chem. 1983, 48, 4, 551–555Publication Date (Print):February 1, 1983Publication History Published online1 May 2002Published inissue 1 February 1983https://pubs.acs.org/doi/10.1021/jo00152a027https://doi.org/10.1021/jo00152a027research-articleACS PublicationsRequest reuse permissionsArticle Views92Altmetric-Citations10LEARN 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 InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
