Are Cyclobutane chains possible?

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SUMMARY

Cyclobutane chains, specifically spiro compounds, are theoretically possible but face significant synthesis challenges due to ring strain. The first compound discussed is spiro[3.3]heptane (C7H12), formed by two cyclobutane units, while the second is dispiro[3.1.3.1]decane (C10H16), formed by three units. The tetrahedral geometry of carbon atoms results in perpendicular ring orientations in these compounds. Despite the theoretical feasibility of longer chains, practical synthesis remains complex.

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  • Cyclobutane chemistry
  • Spiro compound nomenclature
  • Organic synthesis techniques
  • Understanding of ring strain in cyclic compounds
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  • Research spiro[3.3]heptane synthesis methods
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  • Explore the effects of ring strain on cyclobutane derivatives
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Chemists, organic synthesis researchers, and students studying advanced hydrocarbon structures will benefit from this discussion on cyclobutane chains and spiro compounds.

John37309
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Are Cyclobutane chains possible? that's my question.

At least that's 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


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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.
 
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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.
 
Ygggdrasil,
Thank you! Very much appreciated. Thats exactly what i needed. I knew there would be a special name for these chains.

Yes, i realize 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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