53173-41-4

Upstream product

• 5652-90-4 N-methylimide carbonyldichloride 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 108159-95-1 2-[(Z)-Methylimino]-4-[(E)-methylimino]-3-(triphenyl-λ⁵-phosphanylidene)-thietane 

Relevant academic research and scientific papers

Phosphane Alkylenes, 54. - Cumulated Ylides, 21. - A New Way to N-Substituted (Triphenylphosphoranylidene)ketenimines

Reaction of methylenetriphenylphosphorane (1) with isocyanates 5 leads to ylides 6B, which can be methylated at the S atom to give the phosphonium salts 8.Treatment of 8 with sodium methanolate gives rise to formation of the phosphoranes 10, which on treatment with sodium bis(trimethylsilyl)amide undergo β-elimination to form the N-substituted (triphenylphosphoranylidene)ketenimides 3.

Cumulated Ylides, IX. New Synthesis of N-substituted (Triphenylphosphoranylidene)ketenimines and (Triphenylphosphoranylidene)thioketene

Methylenetriphenylphosphorane (1) and isocyanidedichlorides resp. thiophosgene react in the molar ratio 3:1 to give N-substituted (triphenylphosphoranylidene)ketenimines 6A resp. (triphenylphosphoranylidene)thioketene 6B and methyltriphenylphosphonium chloride.The P-Cα-coupling constants in the 13C-NMR-spectra of 6 are in agreement with theoretical calculations.