THE BEHAVIOR OF AZIDO-p-QUINONEIMINES TOWARDS ALKYL PHOSPHITES AND TRIPHENYLPHOSPHINE

ABSTRACT

Triethylphosphite (Ia) reacts with 2-azido-p-benzoquinonedibenzenesulfonimine (IV) in benzene at reflux to produce adducts which have the iminophosphorane structures VIa and VIIa. Only adduct VIb was produced when trimethyl-phosphite (Ib) was allowed to react with IV at the same experimental condition. 2,5-Diazido-p-benzoquinonedibenzenesulfonimine (V) reacts with Ia,b to produce compounds XIVa and XVa in case of Ia and compounds XIVb and XVb in case of Ib. Triphenylphosphine (III) reacts with azide IV to produce compounds VIII and IX and with azide V to produce compound XVII. 2-Amino-p-phenylenedibenzenesulfonamide (X) was produced when diethyl- and/or dimethyl-hydrogen phosphite (IIa,b) reacted with azide IV in benzene at reflux. The phosphoramidate XVIIIa and XVIIIb was produced when a solution of azide IV and the respective phosphite (IIa and/or IIb) in toluene was irradiated using Hg-high pressure lamp in a Pyrex reactor. A mechanism is proposed to explain the formation of these adducts.

Keywords:

• Trialkyl phosphites (I)
• Triphenylphosphine (III)
• Dialkylhydrogen phosphites (II)
• 2-Azido-p-benzoquinonediimine (IV)
• 2,5-Diazido-p-benzoquinonediimine (V)
• Imino-phosphoranes (VI, VII, VIII, IX, XIV, XV and XVI)
• Phosphoramidates (XVIII)
• UV irradiation

Acknowledgments