- Difluorocarbene induced of facile synthesis of chlorohydrins from glycidyl ethers
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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%).
- Singh, Sapna,Bhadury, Pinaki S.,Sharma, Mamta,Palit, Meehir,Jaiswal, Devendra K.
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Read Online
- (Methyl) acrylic acid ether hydroxyl alkane ester synthesis method
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The invention relates to the field of organic synthesis and discloses an (methyl) acrylic acid ether hydroxyl alkane ester synthesis method. The method includes steps: subjecting methyl acrylic acid and epoxy chloropropane to reaction to generate acrylic ester with an epoxy group; subjecting the epoxy group to positioning and ring opening to enable a hydroxyl at 2-site carbon and a sterically hindered ether bond at a 3 site; subjecting to reaction with a primary alcohol compound to generate a target product. The method has advantages that side reactions in a synthesizing process are less, polymer crystallinity can be changed, mechanical performances such as tensile strength of a polymer are enhanced, and the hydrophilic performance can be changed.
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Paragraph 0027; 0028
(2019/08/07)
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- 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
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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.
- Iranpoor, Nasser,Firouzabadi, Habib,Etemadidavan, Elham
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p. 1165 - 1173
(2014/10/16)
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- Facile, high regio- And chemoselective conversion of epoxides to β-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions
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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.
- Aghapour, Ghasem,Afzali, Asieh,Salek, Fahimeh
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experimental part
p. 231 - 236
(2009/12/03)
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- Regioselective synthesis of vic-halo alcohols and symmetrical or unsymmetrical vic-dihalides from epoxides using triphenylphosphine -N-halo imides
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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).
- Iranpoor, Nasser,Firouzabadi, Habib,Azadi, Roya,Ebrahimzadeh, Farzaneh
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- Silphos [PCl3-n (SiO2)n]: A heterogeneous phosphine reagent for the regioselective synthesis of vic-haloalcohols
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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.
- Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
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p. 2615 - 2621
(2007/10/03)
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- Selective conversion of epoxides to vic-halo alcohols and symmetrical or unsymmetrical dihalides by triphenylphosphine/2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) in the presence of quaternary ammonium halides
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A new method is described for the efficient and selective conversion of epoxides to vic-halo alcohols or symmetrical and unsymmetrical dihalides using PPh3/DDQ/R4NX (X = Cl, Br, I) as a mixed-reagent system.
- Iranpoor, Nasser,Firouzabadi, Habib,Aghapour, Ghasem,Nahid, Azarmidokht
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p. 1885 - 1891
(2007/10/03)
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- Reactivity of some carboxylic acids in reactions with some epoxides in the presence chromium (III) ethanoate
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Reactivities have been compared of acetic, acrylic, and methacrylic acid in reactions with epichlorohydrin, phenylglycidyl ether, glycidyl acetate, and glycidyl methacrylate carried in the presence of chromium (III) ethanoate. The acid reactivities changed differently with respect to the oxirane series. The effect of solvents on the reactions of acids with epichlorohydrin has also been observed.
- Bukowska, Agnieszka,Bukowski, Wiktor
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p. 234 - 237
(2013/09/06)
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- The effect of diglyme on the kinetics of chromium(III) ethanoate-catalyzed reactions of carboxylic acids with epichlorohydrin
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The kinetics of reaction between acetic, acrylic, or methacrylic acid and epichlorohydrin in diglyme solution are studied with chromium(III) ethanoate as catalyst. The reaction has been found to be of first-order with respect to both epichlorohydrin and catalyst and zeroth order with respect to acid. Relative reactivities of the acids in reaction with epichlorohydrin and regioselectivity of the addition in diglyme are compared with those for the systems without solvent.
- Bukowski, Wiktor
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- A Convenient Synthesis of Glycidyl Esters (2,3-Epoxypropyl Alkanoates)
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A novel method for synthesizing glycidyl esters (2,3-epoxypropyl alkanoates) 1 has been achieved by the sequence of the organotin phosphate catalyzed reaction of epichlorohydrin 2 with carboxylic acids and dehydrochlorination of the resulting mixture of ester chlorohydrins 3 + 4 followed by separation.
- Otera, Junzo,Matsuzaki, Shinjiro
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p. 1019 - 1020
(2007/10/02)
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