Are Cyclobutane chains possible?

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The discussion centers on the possibility of forming chains of cyclobutane molecules, specifically the idea of linking multiple cyclobutane units together. The initial inquiry presents structures for one, two, and three cyclobutane units, questioning their existence and nomenclature. A participant clarifies that these types of molecules are known as spiro compounds, providing specific names such as spiro[3.3]heptane for two units and dispiro[3.1.3.1]decane for three. While there is no theoretical barrier to creating longer chains, practical synthesis may be challenging due to the significant ring strain present in cyclobutane. Additionally, the importance of understanding carbon's tetrahedral geometry is noted, emphasizing that the rings in spiro compounds are oriented perpendicularly rather than parallel. The original poster expresses gratitude for the clarification and acknowledges the complexities involved in visualizing and synthesizing these structures.
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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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