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      Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis,Trans-Cyclooctadienone Intermediate

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          Abstract

          Electrocyclic ring opening of 4,6-fused cyclobutenamides 1 under thermal conditions leads to cis,trans-cyclooctadienones 2- E, E as transient intermediates, en route to 5,5-bicyclic products 3. Theoretical calculations predict that 4,5-fused cyclobutenamides should likewise undergo thermal ring opening, giving cis,trans-cycloheptadienones, but in this case conversion to 5,4-bicyclic products is thermodynamically disfavored, and these cyclobutenamides instead rearrange to vinyl cyclopentenones.

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          Ynamides: a modern functional group for the new millennium.

          Kyle A DeKorver, Hongyan Li, Andrew G Lohse … (2010)
          Article 0 comments Cited 128 times – based on 0 reviews     Review now
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            Understanding the nature of "superhard graphite"

            Salah Eddine Boulfelfel, Artem Oganov, Stefano Leoni (2012)
            Numerous experiments showed that on cold compression graphite transforms into a new superhard and transparent allotrope. Several structures with different topologies have been proposed for this phase. While experimental data are consistent with these models, the only way to solve this puzzle is to find which structure is kinetically easiest to form. Using state-of-the-art molecular-dynamics transition path sampling simulations, we investigate kinetic pathways of the pressure-induced transformation of graphite to various superhard candidate structures. Unlike hitherto applied methods for elucidating nature of superhard graphite, transition path sampling realistically models nucleation events necessary for physically meaningful transformation kinetics. We demonstrate that nucleation mechanism and kinetics lead to \(M\)-carbon as the final product. \(W\)-carbon, initially competitor to \(M\)-carbon, is ruled out by phase growth. Bct-C\(_4\) structure is not expected to be produced by cold compression due to less probable nucleation and higher barrier of formation.
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              J. Am. Chem. Soc.

              H Hills, G Fu (2012)
              Article 0 comments Cited 8 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (nlm-ta): J Am Chem Soc
                Journal ID (iso-abbrev): J. Am. Chem. Soc
                Journal ID (publisher-id): ja
                Journal ID (coden): jacsat
                Title: Journal of the American Chemical Society
                Publisher: American Chemical Society
                ISSN (Print): 0002-7863
                ISSN (Electronic): 1520-5126
                Publication date PMC-release: 03 July 2015
                Publication date (Electronic): 03 July 2014
                Publication date (Print): 16 July 2014
                Volume: 136
                Issue: 28
                Pages: 9802-9805
                Affiliations
                [† ]Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States
                [‡ ]School of Chemistry and Molecular Biosciences, The University of Queensland , Brisbane, QLD 4072, Australia
                []Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States
                Author notes
                Article
                DOI: 10.1021/ja502252t
                PMC ID: 4353010
                PubMed ID: 24992255
                SO-VID: 85945812-60f1-4222-bff1-0d8f1aa5d719
                Copyright © Copyright © 2014 American Chemical Society
                License:

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                Date received : 04 March 2014
                Funding
                National Institutes of Health, United States
                Categories
                Subject: Communication
                Custom metadata
                document-id-old-9 ja502252t
                document-id-new-14 ja-2014-02252t
                ccc-price

                ScienceOpen disciplines: Chemistry
                Data availability:
                ScienceOpen disciplines: Chemistry

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