Instead, bicyclic amine 17 with an exocyclic double bond was formed (eq 9). 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. 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. 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. journal = "Journal of Organic Chemistry". https://doi.org/10.1016/j.tetlet.2013.01.053. the Altmetric Attention Score and how the score is calculated. Is It Possible to Achieve Organic Superbases beyond the Basicity Limit Using Tetrahedrane Scaffolds?. 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. 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. Find more information on the Altmetric Attention Score and how the score is calculated. The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting

We use cookies to help provide and enhance our service and tailor content and ads. Shintaro Ishida, Kenya Uchida, Takeaki Iwamoto. Lewis acid and iminium cationic activation methods were examined. Osvaldo Gutierrez, Jason G. Harrison, Ryan J. Felix, Fernando Cortés Guzman, Michel R. Gagné, Dean J. Tantillo.

A heavy analogue of the smallest bridgehead alkene stabilized by a base. Your Mendeley pairing has expired. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. 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. Studies on the Friedel–Crafts reaction between carbonyl bicyclic cyclopropane and electronic-rich aromatic systems were conducted. This isn't always the case, as sometimes the fusion of rings induces some extra strain. Fused Tricyclic Phosphiranes—Analysis of Phosphorus Chemical Shieldings.

G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues.

The bicyclic system confers greater ring strain on the β-lactam ring, an aspect important for activity. Ring strain energy in ether- and lactone-containing spiro compounds. © 2005 American Chemical Society. The carboxylic acid group is a possible site of modification to make prodrugs. These metrics are regularly updated to reflect usage leading up to the last few days. 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. Strain in allosteric systems.

By continuing you agree to the use of cookies, Vrije Universiteit Amsterdam data protection policy. redistribute this material, requesters must process their own requests via the RightsLink permission The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. This product is likely formed by isomerization to relieve ring strain. © 2005 American Chemical Society. Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade. Molecular and Electronic Structure of δ-Valerothiolactone. not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information Takeaki Iwamoto, Naohiko Akasaka, Shintaro Ishida.

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. You have to login with your ACS ID befor you can login with your Mendeley account. Mark L. G. Borst, Andreas W. Ehlers, Koop Lammertsma. Robert A. Craig, II, Jennifer L. Roizen, Russell C. Smith, Amanda C. Jones, Scott C. Virgil, Brian M. Stoltz. Powered by Pure, Scopus & Elsevier Fingerprint Engine™ © 2020 Elsevier B.V. We use cookies to help provide and enhance our service and tailor content.

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. jo0513010si20050728_030500.pdf (59.09 kb), http://pubs.acs.org/page/copyright/permissions.html, https://doi.org/10.1016/j.saa.2013.12.029, https://doi.org/10.1007/s11224-012-0186-9, https://doi.org/10.1016/B978-008044992-0.01112-3, https://doi.org/10.1016/B978-008044992-0.01234-7, https://doi.org/10.1016/S0959-6380(07)80008-0.

The ring-opening metathesis (ROM) of some ring-constrained, unsaturated bicyclic frameworks has been studied in the presence of commercially available ruthenium-based catalysts. Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization – how strain associated with bridging affects 5-exo vs. 6-endo selectivity. G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues. Conformational Transferability of the Sulfenyl Carbonyl Group −SC(O)– in Cyclic Thioesters.

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. Deciphering Stability of Five-Membered Heterocyclic Radicals: Balancing Act Between Delocalization and Ring Strain.

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However, a lower yield was obtained in the case of the more highly substituted imine 18. Ehlers and K. Lammertsma". Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles.. Copyright © 2020 Elsevier B.V. or its licensors or contributors. 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. Calculated energies and x,y,z-coordinates of the species discussed. By continuing you agree to the use of cookies. 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). Ryan J. Felix, Colleen Munro-Leighton, and Michel R. Gagné . Matthew K. Stedjan, Joseph D. Augspurger. ; Ehlers, A.W.

© 2005 American Chemical Society. author = "M.L.G. An amide and a carboxylic acid group are also present.

Find more information about Crossref citation counts. 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. Unexpected Formation of Highly Strained 2,5-Dioxa-3-Silabicyclo[2.1.0]Pentane by the Reaction of Isolable Dialkylsilylene with Benzil. 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. abstract = "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. Annual Reports Section "B" (Organic Chemistry). Nahir Y. Dugarte, Mauricio F. Erben, Roland Boese, Mao-Fa Ge, Li Yao, and Carlos O. Della Védova. system. Together they form a unique fingerprint. Conventional strain energies of 1,2-dihydroazete, 2,3-dihydroazete, 1,2-dihydrophosphete, and 2,3-dihydrophosphete. Please reconnect. The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes.

18 publications. 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.

from the ACS website, either in whole or in part, in either machine-readable form or any other form The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring 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.

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. Information about how to use the RightsLink permission system can be found at Borst and A.W. Research output: Contribution to Journal › Article › Academic › peer-review. 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 . 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.

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.

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. 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 about Crossref citation counts. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Dive into the research topics of 'G3(MP2) ring strain in bicyclic phosphorus heterocycles and their hydrocarbon analogues'. Erik P. A. Couzijn, Andreas W. Ehlers, J. Chris Slootweg, Marius Schakel, Steffen Krill, Martin Lutz, Anthony L. Spek, Koop Lammertsma. It was found that the cyclopropane ring-opening was highly dependent on the nature of the counter nucleophile as well as the activation method. @article{28edf95b31d14b95a186b3c825bef7d0. without permission from the American Chemical Society. The influence of cyclopropa(e)nation and heteroatom substitution is analyzed by a comparison with the corresponding bicyclic hydrocarbons and separate ring systems. The calculated strain energies correlate very well with the experimental stability and reactivity of the bicyclic iron-amino phosphirane and phosphirene complexes. Get article recommendations from ACS based on references in your Mendeley library.



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