Triphenylphosphonium Trifluoromethanesulfonate in Reactions with Epoxy Derivatives

Миронов, В. Ф.; Karaseva, A. N.; Nizamov, I. S.; Kedrov, I. S.; Коновалов, А. И.

doi:10.1023/b:rujo.0000044560.16795.94

Cited by 10 publications

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“…Thus, the reaction of triphenylphosphine with epichlorohydrin, recently studied in [168], leads to the oxirane dimerization into a dioxane structure ((1,4-dioxane-2,5-diyl)-bis(methylene))bis(triphenylphosphonium)chloride. The opening of oxirane ring with the formation of triaryl (2-hydroxyalkyl) phosphonium salts occurs in the presence of acids in neutral solvents (alcohols, dichloromethane) [169][170][171][172][173] or during the triarylphosphine reaction in phenol used as the solvent [174].…”

Section: Chemistry 211 Reaction Of Triphenylphosphonium Triflate With Halomethyloxiranesmentioning

confidence: 99%

“…In our work, this approach was applied to a wide range of new oxiranes using the most convenient and stable triphenylphosphonium triflate (1). This compound was easily obtained by mixing triphenylphosphine with trifluoromethanesulfonic acid in dichloromethane [170,173,175]. The signal in the 31 P NMR spectrum of this compound strongly depends on the ratio of reagents.…”

Section: Chemistry 211 Reaction Of Triphenylphosphonium Triflate With Halomethyloxiranesmentioning

confidence: 99%

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Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

et al. 2021

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It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride etherate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolecular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailability and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.

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