ChemInform Abstract: Reductive Activation of Arenes. Part 12. Reaction of the One-Electron Reduction Product of Phthalodinitrile with Butyl Halogenides in Liquid Ammonia.

✍ Scribed by E. V. Panteleeva; I. I. Bil'kis; V. D. Shteingarts

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199919106

✦ Synopsis

Reductive Activation of Arenes. Part 12. Reaction of the One-Electron Reduction Product of Phthalodinitrile with Butyl Halogenides in Liquid Ammonia.

-Reaction of phthalodinitrile with metallic potassium affords the one-electron reduction product which undergoes alkylation at the ipso-or para-position. Main product in all cases is the ipso-substituted analogue (III), disubstitution is only observed for primary butyl halogenides (Ib,c). p-Butyldinitrile (IV) and o,p-dibutylnitrile (V) are proposed to be formed from the same anionic precursor. Their ratio strongly depends on the halogenide counterion. Thus, while for bromide (IIb) the formation of p-butyldinitrile (IVb) predominates, the more reactive iodide (IIc) favors formation of dibutyl derivative (Vc). Formation of compounds (IV) and (V) from one precursor is demonstrated by stepwise alkylation of dinitrile (I) with tert-butyl bromide (IIe) and butyl bromide (IIb). -(PANTELEEVA,