Novel friedel - crafts reactions of some arenes

✍ Scribed by Shashi B. Mahato; Nirup B. Mandal; Anil K. Pal; Swapan K. Mitra

• Book ID: 104205253
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 480 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)90320-5

✦ Synopsis

The novel secondary Friedel-Crafts acylation products of the arenes, dimethyl resorcinol, m-xylene, m-methylanisole and m-chlorotoluene using dichloroacetylchloride and anhydrous AlCIs are described. The formation of the unexpected products has been shown to depend on the nucleophilicity of the arene and the electrophilicity of the acyl carbonyl of the initially formed acylated product. Higher molar proportion of the arene and sometimes elevated temperature are necessary for generation of the products. The reaction pathway has been shown to be incluenced by the formation of the possible complex of AlCls and dichloroacetylchloride with the groups adjacent to the dichloroacetyl function, especially at higher temperature.

Dimethylresorcinol yields the unique products 4, 5, 6, 7 and 9 and m-xylene, m-methylanlsole and mchlorotoluene furnish IO, 13 and 15 respectively.

Electronic factors responsible for generatlon of the products and ratlonalisation of their formation are discussed.