Direct synthesis of polyamides by <i>N</i>‐acyl phosphoramidites

Kawanobe, Wataru; Yamaguchi, Kazuo; Rokicki, Gabriel; Mei, Sha Kei; Yamazaki, Noboru; Nakahama, Seiichi

doi:10.1002/pol.1984.170221008

Cited by 6 publications

(3 citation statements)

References 5 publications

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“…It was in 1969 that poly( m ‐benzamide), one of those polyamides, was first reported to be synthesized by the polycondensation of m ‐aminobenzoyl chloride 1. After that, the polymerization method has been improved: the polycondensation involving thioisocyanates2, 3 and isocyanate,4 and direct polycondensation from m ‐aminobenzoic acid,5–12 and so on. To add more solubility to the polymer, alkylation on the nitrogen of the amide linkage was also investigated 13.…”

Section: Introductionmentioning

confidence: 99%

A variety of poly(m‐benzamide)s with low polydispersities from inductive effect‐assisted chain‐growth polycondensation

Ohishi

Sugi

Yokoyama

et al. 2006

J. Polym. Sci. A Polym. Chem.

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Chain-growth polycondensation of 3-(alkylamino)benzoic acid alkyl esters 1 was investigated for obtaining poly(m-benzamide)s with defined molecular weights and low polydispersities. Polymerization conditions were first studied to find that ethyl 3-(octylamino)benzoate (1b) polymerized in a chain polymerization manner in the presence of lithium 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS) as a base and phenyl 4-methylbenzoate (2b) as an initiator in THF at 0 8C. The molecular weight of the polymer was controlled by the feed ratio of monomer to initiator. The polymerization of 1c-i with a variety of N-alkyl groups was then carried out under the established conditions to yield well-defined poly(m-benzamide)s, which showed higher solubility than those of the corresponding poly(p-benzamide)s. Furthermore, the 4-octyloxybenzyl group on the amide nitrogen in poly1i was removed by treatment with trifluoroacetic acid (TFA) to give N-unsubstituted poly(m-benzamide) (poly1j) with a low polydispersity, which is soluble in DMAc and DMSO, contrary to the para-substituted counterpart. V V C 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 4990-5003, 2006The methyl ester monomer 1a was first polymerized with various bases in the presence of Scheme 1. Inductive effect-assisted chain-growth polycondensation of 1.POLY(m-BENZAMIDE)S WITH LOW POLYDISPERSITIES

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Section: Introductionmentioning

confidence: 99%

A variety of poly(m‐benzamide)s with low polydispersities from inductive effect‐assisted chain‐growth polycondensation

Ohishi

Sugi

Yokoyama

et al. 2006

J. Polym. Sci. A Polym. Chem.

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“…Looking now at the synthesis of fully aromatic polyamides, it is well-known that step-growth condensation polymerization is the main route. − Chain-growth condensation polymerization (CGCP) was also proposed − to give controlled and living characteristics to their synthesis. This approach was also proposed for the synthesis of aromatic poly(ether ketone) for instance …”

Section: Introductionmentioning

confidence: 99%

Simultaneous Anionic Ring-Opening and Condensation Reactions for the Synthesis of Aliphatic–N-Alkyl Aromatic Copolyamides

et al. 2016

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The copolymerization of ε-caprolactam with ethyl 4-(butylamino)benzoate was shown to occur in the presence of sodium salts and an acyllactam as activator in a one-step bulk reaction. The mechanism is based on the deprotonation of the two monomers yielding activated species able to attack an acyllactam or an ester group at the polymer chain ends. Novel copolyamides with different percentages of aromatic/aliphatic units were synthesized in a one-step bulk copolymerization within a few minutes at 140 °C and characterized by NMR spectroscopy, size exclusion chromatography, and thermal analysis (DSC). This methodology, combining simultaneous anionic ring-opening and condensation reactions, affords a new synthetic pathway to introduce an aromatic unit in an aliphatic polyamide backbone, and more specifically a polyamide 6 containing about 20 mol % of N-alkyl aromatic amides was prepared.

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“…Another example has been reported by de Vries [10], where ethylene chlorophosphite was allowed to react with diisopropylamine in dichloromethane giving the cyclic ethylene phosphite ester. This synthetic methodology became popular recently in connection with the synthesis of a library of chiral ligands based on monodentate phosphoramidites [11,12] when stoichiometric amounts of reagents such as chlorodioxa phospholane (4) and diacetylamines are put in contact in the presence of a HCl acceptor (triethylamine) giving finally phosphoramidites (5) (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity

Murzin

Kolesova

2013

Eur. J. Chem.

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KEYWORDSA variety of 2-(N-alkoxy(thio)carbonyl alkyl(aryl)amino)-1,3,2-dioxaphospholanes and phosphorinanes were prepared from chlorodioxaphospholanes and phosphorinanes. Their structures were determined by IR, Mass and NMR spectroscopy. These compounds were employed in direct reactions with elemental sulphur and methylester of chloroacetic acid giving potentially physiologically active N-phosphorylated carbamates with P(O)-N and P(S)N bonds.

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Direct synthesis of polyamides by N‐acyl phosphoramidites

Cited by 6 publications

References 5 publications

A variety of poly(m‐benzamide)s with low polydispersities from inductive effect‐assisted chain‐growth polycondensation

A variety of poly(m‐benzamide)s with low polydispersities from inductive effect‐assisted chain‐growth polycondensation

Simultaneous Anionic Ring-Opening and Condensation Reactions for the Synthesis of Aliphatic–N-Alkyl Aromatic Copolyamides

Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity

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