153032-54-3

Upstream product

• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 153032-51-0 Tetramethyl 1,1,4,4-cyclohexanetetracarboxylate 
• 153032-50-9 Trimethyl 1,1,4-cyclohexanetricarboxylate 

Downstream Products

• 153032-56-5 trans-1,4-Bis(difluoromethyl)-1,4-cyclohexanedimethanol 
• 153032-57-6 trans-1,4-Bis(difluoromethyl)-1,4-bis<<<(trifluoromethyl)sulfonyl>oxy>methyl>cyclohexane 
• 153032-59-8 trans-1,4-Bis(difluoromethyl)-1,4-cyclohexanedicarboxaldehyde 

Relevant academic research and scientific papers

Tetramethyl 1,1,4,4-Cyclohexanetetracarboxylate: Preparation and Conversion to Key Precursors of Fluorinated, Stereochemically Defined Cyclohexanes

Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the litle tetraester 3 affords trans-1,4-dialdehyde 4a as the major product.Fluorination of 4a,b, followed by additional elaboration leads to novel, 1,1,4,4-tetrasubstituted cyclohexanes bearing trans-1,4-difluoromethyl and fluoromethyl groups.The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of dimethyl 1,1-cycloalkyl diesters 7a-c with excess DIBALH results in reduction of only one ester group.An entry into trans-1,4-trifluoromethylated tetrasubstituted cyclohexanes has been gained through stereoselective SF4 fluorination of 1,1,4,4-cyclohexanetetracarboxylic acid 17.Stereochemical assignments are supported by X-ray crystallographic data.