74998-83-7

Upstream product

• 100-52-7 benzaldehyde 
• 948-15-2 {exo-bicyclo[2.2.1]heptan-2-yl}(phenyl)ketone 

Downstream Products

• 74998-81-5 Acetic acid (S)-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl-phenyl-methyl ester 
• 74998-80-4 Acetic acid (R)-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl-phenyl-methyl ester 
• 74998-87-1 Methanesulfonic acid (1R,2R,4S)-bicyclo[2.2.1]hept-2-yl-phenyl-methyl ester 

Relevant academic research and scientific papers

A new method for alkylation of aromatic aldehydes using alkylboron chloride derivatives in the presence of oxygen

Reactions of aromatic aldehydes with alkylboron chloride derivatives in the presence of oxygen have been investigated. Dialkylboron chlorides react with aryl aldehydes to produce arylalkylmethanols in good to excellent yields. Under the same reaction conditions, alkylboron dichlorides lead to the formation of arylalkyl chlorides.

Unconjugated Arylcyclopropanes. Acid-Catalyzed Addition of Acetic Acid to Highly Hindered Arylcyclopropanes

The adduct of 1-naphthylcarbene and norbornene, endo-3-(1-naphthyl)-exo-tricyclo2,4>octane (9) has been prepared. 1H and 13C NMR spectra of this system indicate that the unconjugated arylcyclopropane conformation is favored.Rotation about the naphthyl-cyclopropane bond is restricted.The temperature-dependent NMR indicates a 16.9 kcal/mol barrier to attainment of the conjugated conformation.Acetic acid adds readily under acid catalysis to the phenyl analogue exo-3-phenyl-exo-tricyclo2,4>octane (3) and more slowly to the more strained endo-3-phenyl-exo-tricyclo2,4>octane (4).Kinetic data suggest the involvement of a cationic intermediate with little transition-state charge development at the benzylic carbon.The rates of addition to substituted analogues of 3 and 4 correlate with Hammett ? values, giving ρ values of 2.53 and 2.35, respectively.Product-analysis data support the involvement of a benzylic cation, 23.The slower rate of reaction of the more strained endo isomers has been interpreted in terms of a barrier to attainment of the conjugated conformation which appears to be the favorable conformation for protonation of arylcyclopropanes.This suggestion is supported by the observation that the unconjugated systems, exo- and endo-3-(2,6-dimethylphenyl)-exo-tricyclo-2,4>octanes (27 and 28), add acetic acid 480 and 6.2 x 104 times, respectively, more slowly than 3.