91390-77-1

Upstream product

• 527-53-7 1,2,3,5-Tetramethylbenzene 
• 79-03-8 propionyl chloride 
• 2142-78-1 1-(2,3,4,6-tetramethyl-phenyl)-ethanone 
• 64357-71-7 1-benzoyl-2,3,4,6-tetramethylbenzene 

Downstream Products

• 91390-78-2 1,1-diisodurylpropene 
• 147834-67-1 2,4,5,6-tetramethyl-1-(α-bromopropionyl)benzene 
• 147859-67-4 3-nitro-2,4,5,6-tetramethyl-1-(α-bromopropionyl)benzene 
• 147834-80-8 2-nitromethyl-4,5,6-trimethyl-1-(α-bromopropionyl)benzene 

Relevant academic research and scientific papers

Positional Reactivity of Acylpolymethylbenzenes in Electrophilic Substitution

Friedel-Crafts acylation, bromination, deuteration, and nitration of acetylpentamethylbenzene (APMB), 1-acetyl-2,3,4,6-tetramethylbenzene (ATMB), and 1-benzoyl-2,3,4,6-tetramethylbenzene (BTMB) and the resulting product distribution were investigated.Friedel-Crafts acylation, bromination, and deuteration of APMB and Friedel-Crafts acylation of ATMB gave deacetylation-substitution products.On the other hand, bromination and deuteration of ATMB (or BTMB) and Friedel-Crafts acylation of BTMB gave 5-substituted products.In both cases, the positional reactivities were in accordance with the relative ?-complex stability.Conversely, except for Friedel-Crafts-type nitration, the positional reactivities in the nitration of these substrates were strikingly different from those of the above three reactions.Thus, side-chain functionalization at the 6-methyl group occurred in nitration with fuming nitric acid, depending on the solvents in use.The NMDO calculations and the reaction of APMB with single-electron transfer reagents such as tetranitromethane-hν or cerium(IV) ammonium nitrate suggest that the product distribution in nitration can be explained in terms of a single-electron transfer mechanism.