18072-73-6

Upstream product

• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 18072-55-4 1-Cyan-2-imino-3-phenyl-3-benzyl-cyclohexan 
• 100-39-0 benzyl bromide 

Downstream Products

• 110533-44-3 1-benzyl-1-phenylcyclohexane 
• 102161-91-1 rac-2-benzyl-2-phenylcyclohexan-1-ol 
• 102663-30-9 3-(2-benzyl-2-phenyl-cyclohexyloxy)-propionitrile 
• 102811-78-9 [3-(2-benzyl-2-phenyl-cyclohexyloxy)-propyl]-dimethyl-amine 

Relevant academic research and scientific papers

Synthetic Applications and Mechanistic Studies of the Hydroxide-Mediated Cleavage of Carbon-Carbon Bonds in Ketones

The hydroxide-mediated cleavage of ketones into alkanes and carboxylic acids has been reinvestigated and the substrate scope extended to benzyl carbonyl compounds. The transformation is performed with a 0.05 M ketone solution in refluxing xylene in the presence of 10 equiv of potassium hydroxide. The reaction constitutes a straightforward protocol for the synthesis of certain phenyl-substituted carboxylic acids from 2-phenylcycloalkanones. The mechanism was investigated by kinetic experiments which indicated a first order reaction in hydroxide and a full negative charge in the rate-determining step. The studies were complemented by a theoretical investigation where two possible pathways were characterized by DFT/M06-2X. The calculations showed that the scission takes place by nucleophilic attack of hydroxide on the ketone followed by fragmentation of the resulting oxyanion into the carboxylic acid and a benzyl anion.