140199-75-3

Upstream product

• 1449-46-3 benzyltriphenylphosphonium bromide 
• 99328-15-1 1-trimethylsilyl benzylidene triphenylphosphorane 

Downstream Products

• 140199-82-2 C₂₉H₃₀NP₂⁽¹⁺⁾*Cl^(1-) 
• 164799-64-8 (C₆H₅)3PC(C₆H₅)PCl⁽¹⁺⁾*AlCl₄^(1-)=[(C₆H₅)3PC(C₆H₅)PCl]AlCl₄ 
• 143265-88-7 C₂₅H₂₀P₂Se₂ 
• 143265-91-2 C₂₅H₂₀P₂S₂ 

Relevant academic research and scientific papers

Ylidyl-dihalogenphosphane - Strukturbilder einer sich anbahnenden Dissoziation

The reaction of phosphonium ylides with phosphorus trihalides has been studied for the synthesis of ylidyl-dihalophosphanes (= dihalophosphanyl ylides (Ph3P=CR-PX2 3, X = Cl, and 9, X = Br.Compounds 3, R = aryl, are readily prepared from the phosphonium bromides Br, compounds 3, R = alkyl, SiMe3 or PCl2, and 9 are obtained from silylylides Ph3P=CR-SiMe3, compound 3, R = PPh3(1+) results from the addition of PCl3 to the hexaphenylcarbodiphosphorane.A (β-morpholinovinyl)dichlorophosphane 12 has also been prepared.Ylides 3 are oxidized by sulfur and selenium and are converted to ylidyl-chlorophosphenium (= chlorophosphaalkenyl-phosphonium) salts AlCl4 10.In the 31P-NMR spectra of 3 and 9 the geminal coupling 2JPP indicates the phosphorus lone pair to be synperiplanar to the phosphonio group.In one case the P(III)-C rotation barrier has been estimated from VT-31P-NMR spectra.By X-ray crystallography the structures of 3, R = Me, 2,6-Cl2C6H4, 4-NO2C6H5, PCl2, of 9, R = Me (two molecules), SiMe3, of an ylidyl-selenophosphonyl dichloride (11b), and of 12 have been analyzed.They provide representatives for the full range of rotation from the symmetric conformer with two equal P-X bonds to the conformer with one P-X bond perpendicular to the PCP plane and with this bond being extremely elongated.Thus, they map out the pathway to P-X bond breaking.On this way the initial charge transfer from the ylidic carbon to the antibonding P-X orbital ends up in a ? donation and P-X dissociation. - Key Words: Ylides, dichloro- and dibromophosphanyl-/ Enamines, dichlorophosphanyl-/ Phosphonium ions, chlorophosphaalkenyl-/ Stereoelectronic (anomeric) effect and anionic hyperconjugation

Spontaneous dissociation of phosphoniumylidyl-chlorophosphines to ionic phosphenium chlorides

The products from the replacement of two chlorofunctions of PCl3 by a pair of phosphoniumylidyl substituents or by both a phosphoniumylidyl and an amino substituent are ionic phosphenium chlorides and not covalent chlorophosphines.