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cis,cis,cis-tetramethyl 1,2,4,5-cyclohexanetetracarboxylate

Robinson¹, Hua, Fan

¹Department of Geology, Southern Illinois University-4324, Carbondale, IL 62901, USA. robinson@geo.siu.edu.

Acta Crystallographica. Section C, Crystal Structure Communications

|December 19, 2000

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Researchers synthesized a novel compound, C(14)H(20)O(8), through catalytic hydrogenation. This study details its unique structure with distorted ring angles due to specific substituent positioning.

Area of Science:

Organic Chemistry
Stereochemistry
Catalysis

Background:

Cyclohexane derivatives are fundamental in organic chemistry.
Understanding substituent effects on ring conformation is crucial for predicting chemical properties.

Purpose of the Study:

To synthesize and characterize a novel cyclohexane derivative.
To investigate the impact of multiple methoxycarbonyl substituents on ring geometry.

Main Methods:

Catalytic hydrogenation of tetramethyl 1,4-cyclohexadiene-1,2,4,5-tetracarboxylate.
Characterization of the resulting compound's structure.

Main Results:

Successful synthesis of C(14)H(20)O(8) using palladium/carbon catalyst.

Related Experiment Videos

All four methoxycarbonyl groups were found on the same face of the chair-conformed ring.

Significant ring distortion observed due to 1,3-diaxial methoxycarbonyl groups.

Conclusions:

The synthesis yielded a uniquely distorted cyclohexane structure.
The observed distortion highlights the steric influence of multiple substituents.
This compound serves as a model for studying conformational strain in cyclic systems.