16675-12-0

Upstream product

• 23176-19-4 (diphenylphosphinomethyl)diphenylphosphine selenide 
• 2071-20-7 bis-diphenylphosphinomethane 

Downstream Products

• 23176-19-4 (diphenylphosphinomethyl)diphenylphosphine selenide 
• 140388-90-5 {PtCl(PEt₃)(CH₂(P(Se)Ph₂)2-Se,Se)}ClO₄ 
• 86721-75-7 [C₅H₅Ni(((C₆H₅)2PSe)2(CH₂))]⁽¹⁺⁾*BF₄^(1-)=[C₅H₅Ni(((C₆H₅)2PSe)2(CH₂))]BF₄ 
• 189808-75-1 [(η(6)-p-cymene)RuCl(η(2)-(SePPh2)2CH2-Se,Se')]BF4 

Relevant academic research and scientific papers

Synthesis of Phosphine Chalcogenides Under Solvent-Free Conditions Using a Rotary Ball Mill

The mechanochemical technique of ball milling has been applied to the solventless and eco-friendly synthesis of chalcogenides (sulfide and selenide) of a variety of tertiary and aminophosphines. In most of the cases, the products are obtained in almost quantitative yields with high purity by applying a simple workup procedure without using chromatographic techniques or any other purification methods. The scope of this methodology was explored by using a range of phosphines (mono, di and tetra) to synthesize partial as well as mixed chalcogenides. The use of almost equimolar amounts of starting materials and the absence of any byproducts significantly simplifies the product isolation compared with the standard solution state reactions, thus providing a highly atom economic (100 %) method with an ideal E-factor (E = 0). The solid-state reactions were monitored by 31P{1H} NMR spectroscopy. The structures of some of the products are also confirmed by single-crystal X-ray analyses. Although most of the reactions were carried out on ca. 100-mg scale, the scaling up of the reaction did not affect the course of the reaction.

Rapid Transfer of Selenium from Tertiary Phosphine Selenides to Tertiary Phosphines

Selenium transfer between PR3Se and PR3 in solution is rapid on the n.m.r. time scale, and a bimolecular process is indicated.Mixtures of Ph2P(Se)C2H4(Se)PPh2, Ph2(Se)C2H4PPh2, and Ph2PC2H4PPh2 display similar variable-temperature 1H n.m.r. characteristics and their methylene-proton signals coalesce at elevated temperatures.The compound Ph2P(Se)CH2(Se)PPh2 reacts immediately on mixing with Ph2PCH2PPh2 to give exclusively Ph2P(Se)CH2PPh2, whereas solutions of Ph2P(Se)C2H4(Se)PPh2 and Ph2PC2H4PPh2 equilibrate with Ph2P(Se)C2H4PPh2 in 1:1:2 proportions, respectively.The sulphur analogues behave similarly, but react much more slowly.Selenium reacts at ambient temperature with Ph2P(S)CH2PPh2 to form only Ph2P(S)CH2(Se)PPh2, but the action of sulphur on Ph2P(Se)CH2PPh2 leads to a mixture of Ph2P(Se)CH2(Se)PPh2, Ph2P(Se)CH2(S)PPh2, and Ph2P(S)CH2(S)PPh2.Controlling influences and synthetic implications of these reactions are discussed.