516. Organic fluorides. Part IX. The formation and resolution of α-hydroxy-α-trifluoromethylpropionic acid

Darrall, R. A.; Smith, F.; Stacey, M.; Tatlow, J. C.

doi:10.1039/jr9510002329

Cited by 27 publications

(16 citation statements)

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“…2‐Trifluoromethylacrylic acid (TFMAA),16, 17 t ‐butyl 2‐trifluoromethylacrylate (TBTFMA),4–6 and NBHFA3 were prepared according to the previously described procedure initially and were later supplied by Central Glass (Japan). Other monomers, such as NB, ethyl vinyl ether (EVE), t ‐butyl vinyl ether (TBVE), 3,4‐dihydro‐2‐H‐pyran (DHP), 2,5‐dihydrofuran (DHF), and vinylene carbonate (VC), were obtained from commercial sources and purified by a commonly known procedure.…”

Section: Methodsmentioning

confidence: 99%

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Itô

Okazaki

Miller

2004

J. Polym. Sci. A Polym. Chem.

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Radical copolymerizations of electron-deficient 2-trifluoromethylacrylic (TFMA) monomers, such as 2-trifluoromethylacrylic acid and t-butyl 2-trifluoromethylacrylate (TBTFMA), with electron-rich norbornene derivatives and vinyl ethers with 2,2Ј-azobisisobutyronitrile as the initiator were investigated in detail through the analysis of the kinetics in situ with 1 H NMR and through the determination of the monomer reactivity ratios. The norbornene derivatives used in this study included bicyclo[2.2.1]hept-2-ene (norbornene) and 5-(2-trifluoromethyl-1,1,1-trifluoro-2-hydroxylpropyl)-2-norbornene. The vinyl ether monomers were ethyl vinyl ether, t-butyl vinyl ether, and 3,4-dihydro-2-H-pyran. Vinylene carbonate was found to copolymerize with TBTFMA. Although none of the monomers underwent radical homopolymerization under normal conditions, they copolymerized readily, producing a copolymer containing 60 -70 mol % TFMA. The copolymerization of the TFMA monomer with norbornenes and vinyl ethers deviated from the terminal model and could be described by the penultimate model. The copolymers of TFMA reported in this article were evaluated as chemical amplification resist polymers for the emerging field of 157-nm lithography.

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Section: Methodsmentioning

confidence: 99%

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Itô

Okazaki

Miller

2004

J. Polym. Sci. A Polym. Chem.

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“…Nitroparaffins condense with fluorinated aldehydes and ketones and form ,B-hydroxy derivatives which only unwillingly lose water when heated with strong dehydrating reagents [486,487]: (297) (486) KzCOs . Cyanohydrin synthesis is a very useful means for the synthesis of fluorinated a-hydroxy-acids [488]: CN (298) 1. NaCN, O°C (488] OH Fluorinated ketones having hydrogen atoms on a-carbons undergo regular aldol condensation.…”

Section: Organocopper Compoundsmentioning

confidence: 99%

“…NaCN, O°C (488] OH Fluorinated ketones having hydrogen atoms on a-carbons undergo regular aldol condensation. The aldols are stable, and dehydrate only with difficulty [489]:…”

Section: Organocopper Compoundsmentioning

confidence: 99%

Organic Fluorine Chemistry

Hudlický

1971

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“…Path A indicates that several chiral synthetic or enzymatic approaches have been employed, [5][6][7][8] but these are not commercially attractive. Classical optical resolution using diastereomeric salt formation (Path B) is a viable alternative, [9][10][11][12][13][14] especially if both enantiomers of the acid are desired.…”

Section: Introductionmentioning

confidence: 99%

Tandem crystallization strategies for resolution of 3,3,3‐trifluorolactic acid [CF₃CH(OH)COOH] by chiral benzylamines

et al. 2019

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Resolution of rac‐3,3,3‐trifluorolactic acid by diastereomeric salt formation was reinvestigated. The use of (S)‐1‐phenylethylamine gives coprecipitation of two diastereomeric phases, 1 (S)‐[NH3CH(CH3)Ph](S)‐[CF3CH(OH)COO] and 2 (S)‐[NH3CH(CH3)Ph](R)‐[CF3CH(OH)COO]·H2O. Pure phase 1 may be obtained using molecular sieves as desiccants. Resolution by (S,S)‐2‐amino‐1‐phenylpropan‐1,3‐diol gives monoclinic (S,S)‐[NH3CH(CH2OH)CHOHPh] (R)‐[CF3CH(OH)‐COO] 3 with minor (S)‐3,3,3‐trifluorolactate contamination, which is precluded in the recrystallized orthorhombic form 4. A new resolution using inexpensive phenylglycinol gives pure phase 5 (S)‐[NH3CH(CH2OH)Ph] (S)‐[CF3CH(OH)COO] in 76% yield, 94% ee in a single step, in preference to its (S)‐(R) diastereomer 6. Overall efficient resolution for both enantiomers of the trifluorolactic acid (each ca. 70% yield, 99% ee) may be achieved by various two‐step “tandem” crystallizations, involving direct addition of either water or a second base to the filtrate from the initial reaction.

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516. Organic fluorides. Part IX. The formation and resolution of α-hydroxy-α-trifluoromethylpropionic acid

Cited by 27 publications

References 0 publications

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Organic Fluorine Chemistry

Tandem crystallization strategies for resolution of 3,3,3‐trifluorolactic acid [CF₃CH(OH)COOH] by chiral benzylamines

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516. Organic fluorides. Part IX. The formation and resolution of α-hydroxy-α-trifluoromethylpropionic acid

Cited by 27 publications

References 0 publications

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Organic Fluorine Chemistry

Tandem crystallization strategies for resolution of 3,3,3‐trifluorolactic acid [CF3CH(OH)COOH] by chiral benzylamines

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Product

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Tandem crystallization strategies for resolution of 3,3,3‐trifluorolactic acid [CF₃CH(OH)COOH] by chiral benzylamines