An Unusual Reaction of Triphenylphosphine with Dichlorodinitrobenzofuroxan

Abstract

A novel phosphorylation reaction of dichlorodinitrobenzofuroxan by triphenylphosphine has been studied. An unusual course of the reaction with the participation of benzofuroxan nitro groups as reactive centers has been established. It is shown that as final product of the reaction, a stable diphenolate diphosphabetaine with strong participation of the mesomeric ketoylide structure is formed. The structure of the product has been confirmed by X-ray diffraction.

Keywords:

• Dichlorodinitrobenzofuroxan
• NO generation
• phosphorylation
• triphenylphosphine

Dedicated to Professor Marian Mikołajczyk from the CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

The authors are thankful to Dr. Roland Fröhlich for providing the opportunity to carry out a single crystal X-ray diffraction experiment at the University of Münster.