Generation of tert-Butyl-λ5-phosphanedione and Its Chemical Properties

Stereoselective Syntheses of Organophosphorus Compounds

“…At the same time, all compounds containing the dioxaphosphorane fragment -P(=O)2 are extremely unstable and poorly studied molecules. Only two unstable, inorganic molecules of the dioxophosphorane structure were detected under extreme conditions by physicochemical methods [22]. We found that flash vacuum thermolysis (650 °C, 0.01 mmHg) of trimethylsilyl-tert-butylchlorophosphonate eliminates trimethylchlorosilane and leads to the formation of unstable dioxaphosphorane 1, which is collected in a trap cooled with liquid nitrogen.…”

“…(3) Using alcohol as a reagent, tert-butylphosphonic acid esters were obtained (Figure 4) [22]. The electronegative group deactivates the phosphorus center with respect to electrophilic addition and activates the phosphorus center in the case of nucleophilic addition.…”

“…(2) Compound 8 reacts with styrene oxide to form a [2+3]-cycloaddition product 9, which is a five-membered phosphorus heterocycle, 2-tert-butyl-2-phenyl-1,3,2-dioxophosph olane 10, which was obtained as a mixture two diastereomers in a ratio of 1:2 and purified by distillation under reduced pressure. (3) Using alcohol as a reagent, tert-butylphosphonic acid esters were obtained (Figure 4) [22]. Phosphorylation-dephosphorylation reactions of natural phosphates, such as adenosine triphosphate, which is an important energy-generating molecule that ensures the vital activity of living organisms, proceed through a monomolecular mechanism with the formation of metaphosphate anion [1][2][3].…”

“…(3) Using alcohol as a reagent, tert-butylphosphonic acid esters were obtained (Figure 4) [22]. In S N 2 reactions, the nucleophile cannot attack the negatively charged front reaction center carrying the electron pair, so it attacks the phosphorus from the back side (Figure 5).…”