13183-18-1

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 78-83-1 2-methyl-propan-1-ol 
• 1885-14-9 phenyl chloroformate 
• 539-92-4 diisobutyl carbonate 
• 108-95-2 phenol 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 78-83-1 2-methyl-propan-1-ol 
• 124-38-9 carbon dioxide 
• 108-95-2 phenol 
• 14848-63-6 iso-BuOD 
• 1003-66-3 phenol-d1 

Relevant academic research and scientific papers

Activation of Benzyl Aryl Carbonates: The Role of Cation-π Interactions

Benzyl aryl carbonates can react with a nucleophile to yield an activated electrophile and an aryloxide anion. Previously, we had utilized this in the synthesis of α-nitro esters from nitroalkanes. To further understand the process of activation of these carbonates by nucleophiles, we have performed kinetic studies on the hydrolysis of carbonates using nucleophiles. Rate constants for the hydrolysis were obtained under pseudo-first-order conditions with DABCO as the nucleophile. A comparison of rate constant for hydrolysis of isobutyl phenyl carbonate with benzyl phenyl carbonate shows that the presence of benzyl group results in a 16-fold acceleration of hydrolysis rate. This indicates that the transition state for activation of carbonate is stabilized by cation-π interactions. A comparison of the rate constant for various aromatic rings indicates that electron-donating substituents on the benzyl groups accelerate the rate of hydrolysis. Studies were also carried out with DMAP as nucleophile and the results are presented. Our studies show that stable carbonates can be activated using nucleophiles. Activated acyl groups generated from acid anhydrides have been used in several enantioselective reactions. Our studies show that carbonates can be stable alternatives to acid anhydrides.

METHOD FOR PRODUCING AROMATIC CARBONATE

A method for producing an aromatic carbonate, comprising: (1) performing a reaction between an organometal compound and carbon dioxide to obtain a reaction mixture containing a dialkyl carbonate formed by the reaction,(2) separating the dialkyl carbonate from the reaction mixture to obtain a residual liquid,(3) reacting the residual liquid with an alcohol to form at least one organometal compound and form water and removing the water from the organometal compound, and(4) reacting the dialkyl carbonate separated in step (2) with an aromatic hydroxy compound to obtain an aromatic carbonate.