{\textcopyright} 2005 American Chemical Society.". This article is cited by The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. Shelley A. Smith, Qianyi Cheng, Glake Hill, David H. Magers. Find more information on the Altmetric Attention Score and how the score is calculated. without permission from the American Chemical Society. N2 - The ring strain present in 2-aza-1-phosphabicyclo[n.1.0]alka(e)nes (n = 1-5) is calculated at the G3(MP2) level using homodesmotic reactions. Get article recommendations from ACS based on references in your Mendeley library. Lewis acid and iminium cationic activation methods were examined. Ryan J. Felix, Colleen Munro-Leighton, and Michel R. Gagné . G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes. You’ve supercharged your research process with ACS and Mendeley! Strain in allosteric systems. The ring strain present in 2-aza-1-phosphabicyclo[n.1.0]alka(e)nes (n = 1−5) is calculated at the G3(MP2) level using homodesmotic reactions. The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. Dive into the research topics of 'G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues'. The ring strain present in 2-aza-1-phosphabicyclo[n.1.0]alka(e)nes (n = 1-5) is calculated at the G3(MP2) level using homodesmotic reactions. This product is likely formed by isomerization to relieve ring strain. Studies on the Friedel–Crafts reaction between carbonyl bicyclic cyclopropane and electronic-rich aromatic systems were conducted. Annual Reports Section "B" (Organic Chemistry). https://doi.org/10.1016/j.tetlet.2013.01.053. In all ring structures but one, cyclohexane, substitution by nitrogen and phosphorus is favorable and the effect is most pronounced for the most condensed structures. Ehlers and K. Lammertsma". G3(MP2) Ring Strain in Bicyclic Phosphorus Heterocycles and Their Hydrocarbon Analogues, Department of Chemistry, Faculty of Sciences, Vrije Universiteit, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. The ring-opening metathesis (ROM) of some ring-constrained, unsaturated bicyclic frameworks has been studied in the presence of commercially available ruthenium-based catalysts. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. By continuing you agree to the use of cookies, Vrije Universiteit Amsterdam data protection policy. Research output: Contribution to Journal › Article › Academic › peer-review. In all ring structures but one, cyclohexane, substitution by nitrogen and phosphorus is favorable and the effect is most pronounced for the most condensed structures. from the ACS website, either in whole or in part, in either machine-readable form or any other form The structures of heterocyclic complexes ruled by hydrogen bonds and halogen interactions: Interaction strength and IR modes. This method allowed carbon-carbon bond formation of “non-activated” aziridine via aziridinium ion ring-opening in regio- and stereo-selective manner for the first time. journal = "Journal of Organic Chemistry". ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Studies on the ring-opening of bicyclic cyclopropanes activated by a carbonyl group. Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade. Nahir Y. Dugarte, Mauricio F. Erben, Evamarie Hey-Hawkins, Peter Lönnecke, Sven Stadlbauer, Mao-Fa Ge, Yao Li, Oscar E. Piro, Gustavo A. Echeverría, and Carlos O. Della Védova . Please reconnect. G3(MP2) Ring Strain in Bicyclic Phosphorus Heterocycles and Their Hydrocarbon Analogues.. We reasoned that the ring strain due to the bicyclic system might facilitate ring-opening in the presence of a single carbonyl unit. redistribute this material, requesters must process their own requests via the RightsLink permission However, a lower yield was obtained in the case of the more highly substituted imine 18. Ring strain can be considerably higher in bicyclic systems. The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes. Nahir Y. Dugarte, Mauricio F. Erben, Roland Boese, Mao-Fa Ge, Li Yao, and Carlos O. Della Védova. An amide and a carboxylic acid group are also present. Users are It was found that the cyclopropane ring-opening was highly dependent on the nature of the counter nucleophile as well as the activation method. Find more information about Crossref citation counts. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. Information. Is It Possible to Achieve Organic Superbases beyond the Basicity Limit Using Tetrahedrane Scaffolds?. Fused Tricyclic Phosphiranes—Analysis of Phosphorus Chemical Shieldings. It is shown that the strain caused by fusion with a cyclopropane is the sum of the separate rings, whereas the strain resulting from fusion with cyclopropene leads to strain energies much larger than the sum of rings, as a result of the inverted nature of the bridgehead carbon. This isn't always the case, as sometimes the fusion of rings induces some extra strain. Takeaki Iwamoto, Naohiko Akasaka, Shintaro Ishida. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. These metrics are regularly updated to reflect usage leading up to the last few days. G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues. Electrophilic Pt(II) Complexes: Precision Instruments for the Initiation of Transformations Mediated by the Cation–Olefin Reaction. Electronic Supporting Information files are available without a subscription to ACS Web Editions. In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed. Files available from the ACS website may be downloaded for personal use only. author = "M.L.G. @article{28edf95b31d14b95a186b3c825bef7d0. Alkylative ring-opening of bicyclic aziridinium ion generated from 4-hydroxybutylaziridine with organocopper reagent was achieved successfully to afford 2-alkylsubstituted piperidine in high or moderate yield. Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.. ; Ehlers, A.W. http://pubs.acs.org/page/copyright/permissions.html. Molecular and Electronic Structure of δ-Valerothiolactone. Matthew K. Stedjan, Joseph D. Augspurger. In all ring structures but one, cyclohexane, substitution by nitrogen and phosphorus is favorable and the effect is most pronounced for the most condensed structures. Shintaro Ishida, Kenya Uchida, Takeaki Iwamoto. Copyright © 2020 Elsevier B.V. or its licensors or contributors. the Altmetric Attention Score and how the score is calculated. It is shown that the strain caused by fusion with a cyclopropane is the sum of the separate rings, whereas the strain resulting from fusion with cyclopropene leads to strain energies much larger than the sum of rings, as a result of the inverted nature of the bridgehead carbon. Information about how to use the RightsLink permission system can be found at Ring strain energy in ether- and lactone-containing spiro compounds. The carboxylic acid group is a possible site of modification to make prodrugs. 18 publications. The amount of strain energy in bicyclic systems is commonly the sum of the strain energy in each individual ring. Erik P. A. Couzijn, Andreas W. Ehlers, J. Chris Slootweg, Marius Schakel, Steffen Krill, Martin Lutz, Anthony L. Spek, Koop Lammertsma. Together they form a unique fingerprint. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes. title = "G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues". Bicyclic Systems with Bridgehead (Ring Junction) Phosphorus, Arsenic, Antimony, or Bismuth Atoms. Deciphering Stability of Five-Membered Heterocyclic Radicals: Balancing Act Between Delocalization and Ring Strain. Robert A. Craig, II, Jennifer L. Roizen, Russell C. Smith, Amanda C. Jones, Scott C. Virgil, Brian M. Stoltz. ; Lammertsma, K. T1 - G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues. AB - The ring strain present in 2-aza-1-phosphabicyclo[n.1.0]alka(e)nes (n = 1-5) is calculated at the G3(MP2) level using homodesmotic reactions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. Powered by Pure, Scopus & Elsevier Fingerprint Engine™ © 2020 Elsevier B.V. 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