4638-03-3Relevant academic research and scientific papers
A phosphonium ylide as a visible light organophotoredox catalyst
Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Sakamoto, Tomoyuki,Katsumi, Shiho,Shimizu, Masahiro,Ito, Fuyuki,Suga, Hiroyuki
supporting information, p. 3591 - 3594 (2021/04/14)
A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.
Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
Amerhanova, Syumbelya K.,Dimukhametov, Mudaris N.,Gubaidullin, Aidar T.,Islamov, Daut R.,Litvinov, Igor A.,Lyubina, Anna P.,Mironov, Vladimir F.,Nemtarev, Andrey V.,Pashirova, Tatiana N.,Titov, Eugenii A.,Tsepaeva, Olga V.,Voloshina, Alexandra D.
, (2021/11/01)
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 ether-ate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolec-ular 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 bioavailabil-ity 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.
1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources
Iranpoor, Nasser,Firouzabadi, Habib,Etemadidavan, Elham
, p. 1165 - 1173 (2014/10/16)
1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.
Ionic telomerization of 1-chloro-2,3-epoxypropane with allyl alcohol and properties of products obtained
Kerimov,Orudzheva,Mamedova,Alieva
, p. 1364 - 1369 (2014/01/06)
Ionic telomerization of 1-chloro-2,3-epoxypropane with allyl alcohol in the presence of boron trifluoride etherate as a route to halogenated epoxy oligoethers was studied. Selective chlorination or bromination of the intermediate oligo(chlorohydrin), followed by dehydrochlorination (epoxidation) of the intermediate oligohalohydrins with NaOH, was performed. The synthesized products are effi cient as active diluents for a compound based on ED-20 resin.
Facile, high regio- And chemoselective conversion of epoxides to β-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions
Aghapour, Ghasem,Afzali, Asieh,Salek, Fahimeh
experimental part, p. 231 - 236 (2009/12/03)
A new method is described for the mild and high regioselective conversion of epoxides to β-chlcrohydrins in high yields even in the presence of alcohols, carboxylic acids, oximes, amides, thiols and tetrahydropyranyl ethers using chlorodiphenylphosphine (ClPPh2) under solvent-free and neutral conditions at room temperature and in short reaction times. In addition, some other functional groups such as carbon-carbon double bonds, ester groups and also phenyl ring that are present in the epoxide molecules remain intact in this method.
Silphos [PCl3-n (SiO2)n]: A heterogeneous phosphine reagent for the regioselective synthesis of vic-haloalcohols
Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
, p. 2615 - 2621 (2007/10/03)
Silphos as a silica-based phosphine [PCl3-n (SiO 2)n] provides a practical method for the conversion of epoxides to vic-haloalcohols in the presence of molecular bromine, iodine, or N-halosuccinimides (NXS, X = Cl, Br, I) in CH3CN or under solvent-free conditions at r.t. The simple filtration of heterogeneous Silphos oxide from the reaction mixture affords the pure vic-haloalcohols with excellent yields. Copyright Taylor & Francis Group, LLC.
Regioselective synthesis of vic-halo alcohols and symmetrical or unsymmetrical vic-dihalides from epoxides using triphenylphosphine -N-halo imides
Iranpoor, Nasser,Firouzabadi, Habib,Azadi, Roya,Ebrahimzadeh, Farzaneh
, p. 69 - 75 (2007/10/03)
A simple, novel, and highly regioselective cleavage of epoxides into vicinal halo alcohols and symmetrical or unsymmetrical dihalides is described using different stoichiometries of triphenylphosphine (PPh3) and N-halo succinimide (NXS) or N-halo saccharine (NXSac).
Carbon tetrabromide: An efficient catalyst for regioselective ring opening of epoxides with alcohols and water
Yadav,Reddy,Harikishan,Madan,Narsaiah
, p. 2897 - 2900 (2007/10/03)
Epoxides undergo rapid ring opening with a range of alcohols in the presence of catalytic amount of carbon tetrabromide under mild and convenient conditions to afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with high regioselectivity. Georg Thieme Verlag Stuttgart.
Difluorocarbene induced of facile synthesis of chlorohydrins from glycidyl ethers
Singh, Sapna,Bhadury, Pinaki S.,Sharma, Mamta,Palit, Meehir,Jaiswal, Devendra K.
, p. 1249 - 1253 (2007/10/03)
A novel and unusual approach based on a ClCF2COONa-DMF system has been developed for the synthesis of chlorohydrins via an unexpected mechanism. In a first ever report for the synthesis of chlorohydrins from glycidyl ethers, e.g., CH2=CH-CH2-O-Z, CH 3CH2-O-Z, C6H5-O-Z, C 6H4(o-CH3)-O-Z, CH2=C(CH 3)C(=O)-O-Z, etc., (where Z = glycidyl), difluorocarbene-induced facile regioselective ring opening of epoxides has generated the compound in high yield (70%-83%).
Silica sulfuric acid; an efficient and reusable catalyst for regioselective ring opening of epoxides by alcohols and water
Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Fard, Mohammad Ali Bodaghi
, p. 1113 - 1121 (2007/10/03)
The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of silica sulfuric acid with high degree of regioselectivity. The catalyst is reusable and can be applied several times without any decrease in the yield of reactions.
