The Synthetic Routes of 3-CYCLOHEXYLTHIOPHENE

Synthetic Routes of 3-Cyclohexyltriphenylene: A Comprehensive Review

3-Cyclohexyltriphenylene, commonly referred to as CHT, is a high-performance engineering thermoplastic that possesses excellent mechanical, thermal, and chemical properties.
It is widely used in various applications such as in the automotive, electrical, and medical industries.
The industrial production of CHT relies heavily on the use of synthetic routes, which can be classified into several categories based on the starting materials and the reaction conditions employed.
In this article, we will review the most commonly used synthetic routes for the production of 3-cyclohexyltriphenylene, their advantages, and limitations.

1. Carbon-Carbon Coupling Reactions

One of the most widely used synthetic routes for the production of 3-cyclohexyltriphenylene is through carbon-carbon coupling reactions.
The most common method is the reaction of 1,3-cyclohexadiene with a source of phenyl groups, such as phenylboron or phenyl Grignard reagents.
The reaction typically occurs in the presence of a Lewis acid catalyst, such as aluminum chloride or ferric chloride, and results in the formation of 3-cyclohexyltriphenylene.
This synthetic route is relatively simple and versatile, and offers good yields of the desired product.

2. Halogenation of 1,3-Cyclohexadiene

Another synthetic route for the production of 3-cyclohexyltriphenylene involves the halogenation of 1,3-cyclohexadiene.
This reaction typically involves the treatment of 1,3-cyclohexadiene with a halogenating agent, such as chlorine or bromine, in the presence of a Lewis acid catalyst, such as aluminum chloride or ferric chloride.
The reaction typically results in the formation of 3-chloro- or 3-bromo-1,3-cyclohexadiene, which can then be further transformed into 3-cyclohexyltriphenylene through various reduction and dehydrogenation methods.

3. Olefin Metathesis

Olefin metathesis is another synthetic route for the production of 3-cyclohexyltriphenylene.
This method involves the use of metathesis catalysts, such as ruthenium-based catalysts, to effect the reaction of two alkene molecules, resulting in the formation of a new double bond.
The double bond can then be reduced to a single bond, resulting in the formation of 3-cyclohexyltriphenylene.

4. Ring-Opening Polymerization

Ring-opening polymerization is a synthetic route for the production of 3-cyclohexyltriphenylene that involves the use of metallocene catalysts.
This method involves the reaction of cyclohexene with a metallocene catalyst in the presence of an activator, such as a trialkylaluminum compound.
The reaction typically results in the formation of a cyclohexene polymer, which can then be further transformed into 3-cyclohexyltriphenylene through various reduction and dehydrogenation methods.

Advantages and Limitations of the Synthetic Routes

The synthetic routes for the production of 3-cyclohexyltriphenylene offer various advantages and limitations.
For example, carbon-carbon coupling reactions are relatively simple and versatile, and offer good yields of the desired product.
However, they can also produce unwanted side products, such as 1,3-cyclohexadiene, which can result in lower yields and purity issues.

Halogenation reactions, on the other hand, offer high yields and good purity, but can be more expensive and can produce haz