STUDIES ON PHOSPHONIUM YLIDS—X. THE BEHAVIOUR OF N,N,-2,5-CYCLOHEXADIENE-1,4-DIYLIDENEBIS [BENZAMIDE] TOWARDS WITTIG REAGENTS

Abstract

Methylenetriphenylphosphoranes (2a-b) react with N,N′-2,5-cyclohexadiene-1,4-diylidenebis [benzamide] (1) yielding the new ylid-phosphorane adducts 3a and 3b, respectively. Quinoneimine 1 is reduced mainly to p, -Phenylenedibenzamide (7) when treated with ylid 2c under similar conditions. Structures of the new products were established by analytical and Spectroscopic (IR, ¹H NMR, ³¹P NMR, ¹³C NMR, and MS) results. A mechanism is proposed to explain the formation of compounds 3.

Key Words:

• N,N′-2,5-cyclohexadiene-1,4-diylidenebis(benzamide) 1
• Carbmethoxymethylenetri-phenylphosphorane 2a
• Carbethoxymethylenetriphenylphosphorane 2b
• benzoylmethylenetriphenyl-phosphorane 2c
• Methyl-2,5-bis(benzoylamino)-α-(triphenylphosphoranylidene) benzeneacetate 3a
• Ethyl 2,5-bis(benzoyl-amino)-α-triphenylphosphoranylidene) acetate 3b