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- W2949243322 abstract "Abstract A three-step process for the synthesis of the bis(diorganophosphino)ethanes R 2 PCH 2 CH 2 PR 2 where R=Et, Ph, i Pr, Cy and t Bu was examined. In the first step, diorganochlorophosphines were allowed to react with ethylene glycol in the presence of triethylamine at room temperature in THF solution. For R=Ph, i Pr and Cy, the bisphosphinites R 2 POCH 2 CH 2 OPR 2 were obtained in high yield. For R=Et, the bisphosphinite could not be isolated but may be formed in 80% mixtures with tetraethyldiphosphine, Et 2 PPEt 2 , as a minor component. The reaction of di- t -butylchlorophosphine with ethylene glycol occurs at temperatures greater than 130 °C giving di- t -butyl phosphine oxide, t Bu 2 PH(O), as the only phosphorus-containing product. Thermolysis of the bisphosphinites R 2 POCH 2 CH 2 OPR 2 (R=Ph, i Pr and Cy) at 190–260 °C for 24 h gave the bisphosphine oxides, R 2 P(O)CH 2 CH 2 (O)PR 2 in 9% (Ph), 90% ( i Pr) and 93% (Cy) yields. A DSC study of the thermal rearrangement of Cy 2 POCH 2 CH 2 OPCy 2 to Cy 2 P(O)CH 2 CH 2 (O)PCy 2 yielded an enthalpy of isomerization of −40.4±0.6 kcal mol −1 . Reduction of the bisphosphine oxides, R 2 P(O)CH 2 CH 2 (O)PR 2 (R=Ph, i Pr and Cy) with trichlorosilane gave the bisphosphines, R 2 PCH 2 CH 2 PR 2 in 80–85% yield. The overall yields of the bisphosphines R 2 PCH 2 CH 2 PR 2 (R= i Pr and Cy) in the three-step process were 61 and 75%, respectively, suggesting that this process should be an attractive synthetic pathway to these two bisphosphines." @default.
- W2949243322 created "2019-06-27" @default.
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- W2949243322 date "2010-05-20" @default.
- W2949243322 modified "2023-09-24" @default.
- W2949243322 title "ChemInform Abstract: Synthesis of 1,2-Bis[(diorgano)phosphino]ethanes via Michaelis-Arbuzov Type Rearrangements." @default.
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- W2949243322 doi "https://doi.org/10.1002/chin.200233197" @default.
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