THE NOVEL BEHAVIOR OF DIALKYL PHOSPHITES TOWARD 1,4-BENZOQUINONE MONOIMINES

Diethyl phosphite 2a reacts with N-(phenylsulfonyl)-1,4-benzoquinone monoimine is to give 1,4-diethyl {(2-hydroxy-5-[(phenylsulfonyl)amino]phenyl) bisphosphonate 3a, diethyl {1-hydroxy-4-phenylsulfonyl)imino]-2.5-cyclohexadiene)}phosphonate 3b and amide 3c, respectively When quinone monoimine 1a was reacted with dimethyl- and diisopropyl phosphites (2b,c), the corresponding dialkyl phosphonate adducts 3e and 3f were obtained . Whereas quinone monoimine 1b is reduced mainly to amide 4b when treated with diethyl phosphite 2a, it reacts with dimethyl phosphite 2b to give the dialkyl phosphonate adduct 4a together with amide 4b. Possible reaction mechanism are considered and the structural assignments are based on compatible analytical and spectroscopic results.