Synthesis and characterization of new imidophosphanes and phosphine oxides containing 3,3,4,4-tetramethylsuccinimidyl group

A series of new imidophosphanes and phosphine oxides containing 3,3,4,4-tetramethylsuccinimidyl group were synthesized and characterized by 1H, 13C{1H} and 31P NMR spectroscopy, IR and MS. PhmPCln (m = 3 − n, n = 3, 2, 1) reacted with 3,3,4,4-tetramethylsuccinimide (TH) and potassium 3,3,4,4-tetramethylsuccinimidate 1 to give corresponding PhmPTn. Molecular structures of products were established by single-crystal X-ray diffraction experiments. Attempts to prepare new imidophosphoranes by reactions of 1 with PhmPCln (m = 5 − n, n = 4, 3, 2) resulted in phosphine oxides. In these reactions the phosphoryl group was formed and we characterized a by-product of this type of reaction.

Graphical abstractThe first succinimide derivatives of phosphorus halides whose molecular structures were confirmed by X-ray diffraction have been obtained by reactions of potassium salt of 3,3,4,4-tetramethylsuccinimide with PCl3. Reactions with chlorophenylphosphoranes resulted in phosphine oxides and interesting bicyclic by-product.Figure optionsDownload full-size imageDownload as PowerPoint slide