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Mendeleev Communications, 1994, Volume 4, Issue 3, Pages 85–88
DOI: https://doi.org/10.1070/MC1994v004n03ABEH000358
(Mi mendc5162)
 

This article is cited in 10 scientific papers (total in 10 papers)

1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring

I. E. Mikhailova, G. A. Dushenkoa, A. V. Kisinb, C. Mueggec, A. Zschunked, V. I. Minkina

a Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
b State Scientific Research Institute of Chemistry and Technology of Organoelement Compounds, Moscow, Russian Federation
c Department of Chemistry, Humboldt University, Berlin, Germany
d Federal Institute for Materials Research and Testing, Berlin, Germany
Abstract: Intramolecular rearrangement due to successive 1,5-sigmatropic shifts of chlorine over a five-membered ring were found to occur in 5-chloro-1-alky1-2,3,4,5-tetramethoxycarbonylcyclopentadienes with energy barriers to chlorine migration falling in the range 26.0–27.3 kcal mol–1.
Document Type: Article
Language: English


Citation: I. E. Mikhailov, G. A. Dushenko, A. V. Kisin, C. Muegge, A. Zschunke, V. I. Minkin, “1,5-Sigmatropic Shifts of Chlorine in the Cyclopentadiene Ring”, Mendeleev Commun., 4:3 (1994), 85–88
Linking options:
  • https://www.mathnet.ru/eng/mendc5162
  • https://www.mathnet.ru/eng/mendc/v4/i3/p85
  • This publication is cited in the following 10 articles:
    1. I. E. Mikhailov, G. A. Dushenko, V. I. Minkin, “Pentacarboxycyclopentadienes in Organic Synthesis”, Russ J Org Chem, 57:11 (2021), 1757  crossref
    2. G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “3,3-Sigmatropic Shifts of Allyl Group Along Cyclopentadiene Ring Perimeter”, Russ J Gen Chem, 90:2 (2020), 161  crossref
    3. G.A. Dushenko, I.E. Mikhailov, O.I. Mikhailova, R.M. Minyaev, V.I. Minkin, “STROENIE I?FLUKTUIRUYuSchEE POVEDENIE PENTAMETOKSIKARBONILTsIKLOPENTADIENA, “Doklady Akademii nauk””, Doklady Akademii Nauk, 2017, no. 6, 648  crossref
    4. G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Structure and fluxional behavior of pentamethoxycarbonylcyclopentadiene”, Dokl Chem, 476:2 (2017), 230  crossref
    5. G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin, “Mechanisms of circumambulatory rearrangements of 5-halogeno-1,2,3,4,5-pentamethoxycarbonylcyclopentadienes”, Russ Chem Bull, 64:9 (2015), 2043  crossref
    6. Sergei M. Lukyanov, Alla V. Koblik, Patai's Chemistry of Functional Groups, 2009  crossref
    7. Do Hyong Kim, James A. Mulholland, Jae-Yong Ryu, “Formation of polychlorinated naphthalenes from chlorophenols”, Proceedings of the Combustion Institute, 30:1 (2005), 1245  crossref
    8. A. A. Bumber, G. A. Dushenko, I. A. Profatilova, A. A. Arutyunyants, I. E. Mikhailov, “Electrochemical conversions of pentaphenyl(methoxycarbonyl)cyclopentadiene derivatives”, Russ J Electrochem, 36:5 (2000), 553  crossref
    9. Vladimir I. Minkin, Ruslan M. Minyaev, Igor V. Dorogan, “Computational modeling of the mechanisms of circumambulatory rearrangements of main-group migrants in the cyclopropene ring”, Journal of Molecular Structure: THEOCHEM, 398-399 (1997), 237  crossref
    10. Rainer Koch, Ming Wah Wong, Curt Wentrup, “Facile 1,3- and 1,5-Chlorine Migration”, J. Org. Chem., 61:20 (1996), 6809  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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