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A facile method for the synthesis of β-functionalized ethyldiphenylphosphine oxides is developed based on readily available 2-phenoxyethyldiphenylphosphine oxide used as an equivalent of diphenylvi...

Pentadentate bis[N-alkyl-N-(2-diphenylphosphinylethyl)]diglycolamides [Ph2P(O)CH2CH2N(R)· C(O)CH2]2O, where R Me, Bu, Oct, were synthesized by reaction of diglycolyl chloride with N-alkyl-N-(2-diphenylphosphinylethyl)amines Ph2P(O)CH2CH2NHR obtained by reacting diphenyl(2-phenoxyethyl)phosphine oxide with primary alkylamines in DMSO in the presence of an aqueous alkali. Structure of the prepared compounds was studied by 1H, 13C, and 31P NMR spectroscopy.

According to IR and 15N NMR spectroscopy data, bis(3-aminophenyl)phosphinic acid exists in the molecular form in the DMSO and DMF solutions. The molecular and ionic forms are in equilibrium in the solutions of triethylammonium salt of bis(3-aminophenyl)phosphinic acid in DMSO and DMF.

A series of acyclic symmetric quaternary ammonium chlorides Me2(HOCH2CH2)N+(CH2CH2O)nR Cl– (n = 1, R = n-C9H19; n = 2, R = n-C6H13; n = 3, R = n-C3H7) was synthesized by alkylation of the corresponding tertiary amines Me2N(CH2CH2O)nR with ethylene chlorohydrin in a two-phase system, using water as a solvent. The tertiary amines were synthesized in a heterogeneous system organic phase—aqueous phase, using an aqueous solution of Me2NH and a solid alkali. The intermediate monoethers of ethylene, diand triethylene glycol were obtained in high yield via a phase-transfer alkylation in dioxane, using solid KOH. The proton and carbon atom signals in the NMR spectra of the synthesized amines and ammonium chlorides were assigned based on the data of heteronuclear correlations (1H, 13C).

Homoand heteronuclear NMR experiments (COSY, HSQC, and HMBC) were used for the attribution of the proton and carbon atom signals in the 1H and 13C NMR spectra of N-(ωalkoxyethyl)-N-(2-hydroxyethyl-)N, N-dimethylammonium chlorides Me2(HOCH2CH2)N+(CH2CH2O)nRCl– (n = 1, R = C9H19, C12H25; n = 2, R = C6H13, C12H25; n = 3, R = C3H7) bearing either one, two or three ethylene glycol units in 12-, 15-, and 18-membered substituents at the nitrogen atom. Performed experiments unambiguously confirmed the structures of the ammonium chloride studied.