10395-50-3

Upstream product

• 67-56-1 methanol 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 124287-80-5 3,3-dimethylnorboranone ketal 
• 1323371-30-7 6-O-allyl-3,4,5-tri-O-benzyl-1,2-O-{(+)-1,7,7-trimethyl[2,2,1]bicyclohepta-6-ylidene}-D-myo-inositol 

Relevant academic research and scientific papers

Photochemical acetalization of carbonyl compounds in protic media using an in situ generated photocatalyst

Carbonyl compounds are conveniently converted into their corresponding dimethyl acetals in good yields and short reaction times by means of a photochemical reaction in methanol with a catalytic amount of chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone, CA) as the sensitizer. Using aldehydes gives better results than using ketones, which also tend to form enol ethers as side products. These results are similar to those of simple acid-catalyzed acetalization reactions, suggesting the involvement of a photochemically generated acid. On the basis of steady state and laser flash photolysis data the reaction is proposed to involve the in situ generation of a photocatalyst (2,3,5,6-tetrachloro-1,4-hydroquinone, TCHQ) via reaction of CA with the solvent. The acetalization process is initiated by ionization of TCHQ, followed by loss of a proton to the solvent or the carbonyl, which starts a catalytic reaction. The photocatalyst is regenerated via a disproportionation reaction.

Thermochemical Studies of Carbonyl Reactions. 4. Enthalpies of Hydrolysis of Norbornyl Ketals

The dimethyl ketals of norbornanone and of eight methyl-substituted norbornanones were prepared, and the enthalpies of hydrolysis were determined.The compounds were chosen to provide a variety of steric interactions between the methyl substituents and the ketal group, much of which would be relieved on going to the ketone.The enthalpies of reaction varied by over 4 kcal/mol.The experimental data were modeled by molecular mechanics (MM2), and although a good correlation was found for the less substituted compounds, the ketal of camphor fell off the slope = 1 correlation line.The free energy changes were determined, and were found not to be well correlated with the enthalpy changes.