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Are Cyclobutane chains possible?

  1. Jan 8, 2012 #1
    Are Cyclobutane chains possible? thats my question.

    At least thats what i have been calling these chains.

    This is 1 normal Cyclobutane; C4H8

    100px-Cyclobutane-buckled-3D-balls.png

    This might be 2 Cyclobutane's chained together; C7H12

    2-cyclobutane.png

    This might be 3 Cyclobutane's chained together; C10H16

    3-cyclobutane.png

    ------

    So i'm asking the question is it possible to form these chains? I can't find any information about these molecules. But maybe its because i'm calling them the wrong thing. Maybe these hydrocarbons have a special name. Or does anyone know why i can't seem to find any info about these type of molecules? I have suggested a chain of 2 Cyclobutane's or 3 Cyclobutane's, but in theory, maybe its possible for many more of these molecules to chain together?, Maybe 6 or 7 of them chained together in a similar fashion.

    Thanks Guys,
    John.
     
  2. jcsd
  3. Jan 8, 2012 #2

    Ygggdrasil

    User Avatar
    Science Advisor

    These types of molecules are called spiro compounds. The first is called spiro[3.3]heptane and the second is called dispiro[3.1.3.1]decane. Although I don't see any theoretical reason why a chain of arbitrary length could not exist, in practice it may be difficult to synthesize such chains as the cyclobutane rings contain significant amounts of ring strain.

    Also, in your 3D models, remember that carbon atoms have a tetrahedral geometry. In spiro[3.3]heptane, the two rings will be perpendicular, not parallel.
     
  4. Jan 9, 2012 #3
    Ygggdrasil,
    Thank you! Very much appreciated. Thats exactly what i needed. I knew there would be a special name for these chains.

    Yes, i realise these chains would be under significant strain and could be difficult to synthesise.

    As for the images, yes, i know they are wrong and in reality ever second square would twist through 90 degrees.

    You have been been very helpful to me Ygggdrasil, thank you my friend!

    John.
     
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