The Reaction of Bis[4-(p-substituted anilino)-3-penten-2-onato]copper(II) with Benzoyl chloride

Abstract

The reaction of bis[4-(p-substituted anilino)-3-penten-2-onato]copper(II) [1] with benzoyl chloride has been investigated. The substituents are a: H, b: CHc: OCH8, and d: Cl. [1] reacted with benzoyl chloride(2.1 molar to C/D) in benzene at 20-25° C for 1-4.5 hours to give 3-benzoyl-4-p-substituted anilino-3-penten-2-one [2] (63-66% yield), 4'-substituted benzanilide [3] (trace), 3-chloro-4-p-substituted anilino-3-penten-2-one [4] (5'9%), and cuprous chloride. In the presence of pyridine (2.0 molar), the reaction of [1 a] or [1 c] with benzoyl chloride gave [2 a] or [2 c] in 82-L/85% yield and trace of [3 a] or [3c] together with dichlorobis (pyridine)copper [1] in place of cuprous chloride. The reaction of [1 c] with cupric chloride (2.1 molar) gave [4 c] in 10% yield and cuprous chloride. A mechanism for the reaction of [1] with benzoyl chloride is discussed.