ChemInform Abstract: Reactions of Phosphites with 1,4-Benzoquinone Monoimines

Trimethyl phosphite (2a) reacts with N-(phenylsulfonyl)-1,4-benzoquinone monoimine (1a) to give the respective phosphonate 3c, phosphates 3d, 3e and the alkylated products 3a and 3b. The reaction of triethyl phosphite (2b) with the same quinone imine 1a yields only the phosphate adduct 3f and the amide 3g. Triisopropyl phosphite (2c) reacts with 1a to form the alkylated product 3h. Trimethyl phosphite (2a) gives the phosphate 4a on reaction with N-(methylsulfonyl)- 1,4-benzoquinone monoimine (1b). In case of the reaction of triethyl and triisopropyl phosphites (2b, c) with 1b only the respective alkylated products 4b–d are obtained. A mechanism is proposed to explain the formation of the new adducts.