Ueber trishydrofluoride tertiaerer amine und ihren einsatz als fluorierungsmittel

Synthesis of Symmetrical Bis-(2-chloro-1,3,2-benzodiazaphosphorinones) Hydrolysis and Fluorination of Selected Compounds

“…In the 1 H-NMR spectra of these new compounds, the resonance of the NCH 3 protons occurs at about 2.85 ppm as a singlet. In the 13 C-NMR spectra, both the NCH 3 and C=O resonance are singlets, as expected, at about 43 ppm and 164 ppm, respectively. The introduction of the spacer -(CH 2 ) n -into the molecule does not significantly affect the d( 13 C) value of the (C=O) group.…”

“…In the 1 H-NMR spectrum of 5 c, one doublet due to PNCH 3 ( 3 J(PH) = 9.29 Hz) was observed. In the 13 C-NMR spectrum of 5 c, only one doublet at 30.98 ppm (PNCH 3 ) with The reactive P±Cl derivatives can easily be fluorinated, using NaF, KF, ZnF 2 [12], or trialkylamine trihydrofluorides R 3 N´3 HF (R = Me, Et, n-Pr, etc) [13]. Et 3 N´3 HF has been successfully used in the fluorination of organochlorophosphines.…”

“…A sharp signal in the 31 P-NMR spectrum at 127 ppm was observed after extended pulsing. However, due to the very low solubility in common solvents, no satisfactory 1 H-NMR and 13 C-NMR spectra were available. No clear coupling constants could be identified.…”

Regio- and stereoselective synthesis of vicinal fluorohydrins

“…Triethylamine trihydrofluoride (Et 3 NÁ3HF) [83] is a mild reagent, which is thermostable until about 150 8C and can be used in glassware for a variety of fluorination methods [73,84,85]. The reagent was originally synthesized by Aranda et al and used in situ for opening of epoxides [86][87][88].…”

“…The reagent was originally synthesized by Aranda et al and used in situ for opening of epoxides [86][87][88]. Heating of 10,11-epoxy-undecanoate with the neat reagent [83] at 100 8C for 36 h gave a 45:55 mixture of the abovementioned fluorohydrins in 77% yield [77]. Ring opening of symmetric epoxides with Et 3 NÁ3HF was shown to be highly stereoselective.…”