18780-05-7

Upstream product

• 2040-01-9 2',3',4',5',6'-pentamethylacetophenone 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 700-12-9 pentamethylbenzene, 
• 103224-96-0 (4-Chloro-phenyl)-(2,3,4,5-tetramethyl-6-nitromethyl-phenyl)-methanone 
• 13389-51-0 (3-chlorophenyl)(4-methoxyphenyl)methanone 
• 78589-10-3 (4-chlorophenyl)(2-methoxyphenyl)methanone 
• 105038-04-8 trideuterioacetylpentamethylbenzene 

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.