Jump to main content
Jump to site search
Publishing
Advanced

Issue 19, 1985
Previous Article Next Article

Cleavage of 5-nitro-2-(trimethylsilylmethyl)thiophene by methanolic sodium methoxide. U.v. spectroscopic and solvent isotope effect evidence for generation of the anion [5-O2N·C4H2S· CH2-2]–

Pasquale Dembech,  Colin Eaborn  and  Giancarlo Seconi 

Abstract

The reaction of 5-nitro-2-(trimethylsilylmethyl)thiophene with NaOMe–MeOH involves generation of the observable anion [5-O2N·C4H2S· CH2]– with a solvent isotope effect k(MeOH)/k(MeOD) of 0.5, followed by protonation of the anion with a solvent isotope effect of 10; the results confirm that cleavages of RSiMe3 compounds by NaOMe–MeOH involve separation of the anions R–, and that the isotope effect in the reaction of R– with MeOH depends greatly on the degree of conjugative delocalization of the negative, not just on the acidity of Rh.

Back to tab navigation
Download options Please wait...

Article type: Paper
DOI: 10.1039/C39850001289
Citation: J. Chem. Soc., Chem. Commun., 1985,0, 1289-1290
  •   Request permissions

    Cleavage of 5-nitro-2-(trimethylsilylmethyl)thiophene by methanolic sodium methoxide. U.v. spectroscopic and solvent isotope effect evidence for generation of the anion [5-O2N·C4H2S· CH2-2]–

    P. Dembech, C. Eaborn and G. Seconi, J. Chem. Soc., Chem. Commun., 1985, 0, 1289
    DOI: 10.1039/C39850001289

    If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

    Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
    • For reproduction of material from PCCP:
      Reproduced from Ref. XX with permission from the PCCP Owner Societies.
    • For reproduction of material from PPS:
      Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
    • For reproduction of material from all other RSC journals and books:
      Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

    If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

    In all cases the Ref. XX is the XXth reference in the list of references.

    If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
    • For reproduction of material from PCCP:
      [Original citation] - Reproduced by permission of the PCCP Owner Societies
    • For reproduction of material from PPS:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
    • For reproduction of material from all other RSC journals:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry

    If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements