Isatin Imines in the Reaction with Iminophosphine: X-Ray Structure of Phospholane Derivatives

Abstract

3-Imino-1-methyl-indolin-2-one (2a) reacts with phosphorus hexamethyltriamide 1(1:1 mol) in dry toluene at room temperature to give the dimeric spirophospholane 4a. On the other hand, the reaction of 3-(4-arylimino)-1-methylindoline-2-ones 2b–2c with trisdimethylaminophosphine 1 in boiling toluene gave phosphoramides 4b and 4c. Furthermore, 1-benzyl-3-(4-arylimino)indolin-2-ones 3a–3c react with aminophosphine 1 in excess as solvent at 110 °C for 6–8 h to give phosphonamides 5a–5c. Possible reaction mechanism are considered and the structural assignments are based on spectroscopic data and x-ray analysis.

GRAPHICAL ABSTRACT

Keywords:

• Dimeric spirophospholane
• dimethylphosphoramides
• 1-isatin-3-imine derivatives
• phosphorus hexamethyltriamide

ACKNOWLEDGMENTS

We thank Ibrahim S. A. Farag, Department of Solid State Physics, National Research Centre, Giza, Egypt, and his coworker for doing X-ray diffraction analysis.