Are Cyclobutane chains possible?

  • Thread starter John37309
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In summary, these chains are called spiro compounds and can contain arbitrary lengths of cyclobutane rings, but it may be difficult to synthesize due to ring strain. The correct names for the two chains mentioned are spiro[3.3]heptane and dispiro[3.1.3.1]decane. Additionally, the 3D models may not accurately represent the actual structure, as the carbon atoms have a tetrahedral geometry. Overall, these chains are known to be under significant strain and may be challenging to produce in practice.
  • #1
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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  • #2
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.
 
  • #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 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.
 

1. Are cyclobutane chains stable?

Yes, cyclobutane chains are stable. They are able to maintain their structure due to the strength of the carbon-carbon bonds. However, they are less stable than other cycloalkanes such as cyclohexane.

2. Can cyclobutane chains exist in nature?

Yes, cyclobutane chains can exist in nature. They are commonly found in plants and animals, and are also present in some natural products such as steroids.

3. How are cyclobutane chains formed?

Cyclobutane chains can be formed through various chemical reactions, such as the addition of two double bonds in a butane molecule. They can also be formed through photochemical reactions or through the rearrangement of other cycloalkanes.

4. What are the properties of cyclobutane chains?

Cyclobutane chains have a tetrahedral geometry, with bond angles of approximately 109.5 degrees. They are also relatively rigid and have a high melting point compared to other cycloalkanes. They are less reactive than cyclopropane due to the increased strain on the carbon-carbon bonds.

5. Are there any practical applications of cyclobutane chains?

Yes, cyclobutane chains have various practical applications. They are used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. They also have potential uses in materials science and as building blocks for organic synthesis.

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