Jump to main content
Jump to site search
Publishing
Advanced

Issue 1, 1998
Previous Article Next Article

Medium-sized cyclophanes. Part 46.1 The preparation and novel [3.3]- and [1.5]-sigmatropic rearrangements of [n.2]cyclophanes having a spiro skeleton †

Takehiko Yamato,  Jun-ichi Matsumoto  and  Koji Fujita 

Abstract

Oxidation of dihydroxy[n.2]metacyclophanes 4 with K3[Fe(CN)6] affords in good yield the intramolecular O–C coupling products 5 having a spiro skeleton. Variable temperature 1H NMR measurements indicate that compounds 5 are interconvertible by thermal [3.3]sigmatropic rearrangement. The free energies for the [3.3]sigmatropic rearrangement increase with increasing length of the methylene bridge in compounds 5. The substituent effect on the [1.5]sigmatropic rearrangement of [2.2]cyclophanes 3 having a spiro skeleton is also discussed.

Back to tab navigation
Download options Please wait...

Article type: Paper
DOI: 10.1039/A704105E
Citation: J. Chem. Soc., Perkin Trans. 1, 1998,0, 123-130
  •   Request permissions

    Medium-sized cyclophanes. Part 46.1 The preparation and novel [3.3]- and [1.5]-sigmatropic rearrangements of [n.2]cyclophanes having a spiro skeleton †

    T. Yamato, J. Matsumoto and K. Fujita, J. Chem. Soc., Perkin Trans. 1, 1998, 0, 123
    DOI: 10.1039/A704105E

    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