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Mannich Condensation of o‐ Phthalaldehyde...

Bill, J. C., Tarbell, D. S. 2003. o-Phthalaldehyde . Organic Syntheses. 82.

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Synthesis and biological activity of disubstituted n-alkylbenzenes.

N2 - We recently reported the cationic polymerization of o-phthalaldehyde to macrocyclic poly(phthalaldehyde) polymers. Resubjecting the cyclic polymers to the polymerization conditions led to a redistribution of the polymer to a new cyclic structure consistent with thermodynamic equilibrium. We now report the synthesis of cyclic poly(phthalaldehyde) derivatives and demonstrate the scrambling of distinct homopolymer mixtures to copolymers under the cationic polymerization conditions. Homopolymer mixtures are found to rapidly redistribute, first to multiblock cyclic copolymers. With extended reaction time, random macrocyclic copolymers are obtained. Evolution of the microstructure was monitored by NMR spectroscopy, MALDI-TOF mass spectrometry, and gel permeation chromatography (GPC). The reported scrambling method leads to the rapid preparation of macrocyclic copolymers of high molecular weight with variable microstructure depending on reaction times and catalyst loadings.

06/04/2009 · Synthesis of 1,2-disubstituted isoindoles from o-phthalaldehyde and ..

AB - We recently reported the cationic polymerization of o-phthalaldehyde to macrocyclic poly(phthalaldehyde) polymers. Resubjecting the cyclic polymers to the polymerization conditions led to a redistribution of the polymer to a new cyclic structure consistent with thermodynamic equilibrium. We now report the synthesis of cyclic poly(phthalaldehyde) derivatives and demonstrate the scrambling of distinct homopolymer mixtures to copolymers under the cationic polymerization conditions. Homopolymer mixtures are found to rapidly redistribute, first to multiblock cyclic copolymers. With extended reaction time, random macrocyclic copolymers are obtained. Evolution of the microstructure was monitored by NMR spectroscopy, MALDI-TOF mass spectrometry, and gel permeation chromatography (GPC). The reported scrambling method leads to the rapid preparation of macrocyclic copolymers of high molecular weight with variable microstructure depending on reaction times and catalyst loadings.

Catalyst-free synthesis of isoindolin-1 ..

Synthesis and structure-activity relationships of 5,6-dimethoxy-N-alkyl- and N-alkylaryl-substituted 2-aminoindans.

AB - End-capped poly(phthalaldehyde) (PPA) synthesized by anionic polymerization has garnered significant interest due to its ease of synthesis and rapid depolymerization. However, alternative ionic polymerizations to produce PPA have been largely unexplored. In this report, we demonstrate that a cationic polymerization of o-phthalaldehyde initiated by boron trifluoride results in cyclic PPA in high yield, with high molecular weight, and with extremely high cyclic purity. The cyclic structure is confirmed by NMR spectroscopy, MALDI-TOF mass spectrometry, and triple-detection GPC. The cyclic polymers are reversibly opened and closed under the polymerization conditions. Owing to PPA's low ceiling temperature, cyclic PPA is capable of chain extension to larger molecular weights, controlled depolymerization to smaller molecular weights, or dynamic intermixing with other polymer chains, both cyclics and end-capped linears. These unusual properties endow the system with great flexibility in the synthesis and isolation of pure cyclic polymers of high molecular weight. Further, we speculate that the absence of end groups enhances the stability of cyclic PPA and makes it an attractive candidate for lithographic applications.

N2 - End-capped poly(phthalaldehyde) (PPA) synthesized by anionic polymerization has garnered significant interest due to its ease of synthesis and rapid depolymerization. However, alternative ionic polymerizations to produce PPA have been largely unexplored. In this report, we demonstrate that a cationic polymerization of o-phthalaldehyde initiated by boron trifluoride results in cyclic PPA in high yield, with high molecular weight, and with extremely high cyclic purity. The cyclic structure is confirmed by NMR spectroscopy, MALDI-TOF mass spectrometry, and triple-detection GPC. The cyclic polymers are reversibly opened and closed under the polymerization conditions. Owing to PPA's low ceiling temperature, cyclic PPA is capable of chain extension to larger molecular weights, controlled depolymerization to smaller molecular weights, or dynamic intermixing with other polymer chains, both cyclics and end-capped linears. These unusual properties endow the system with great flexibility in the synthesis and isolation of pure cyclic polymers of high molecular weight. Further, we speculate that the absence of end groups enhances the stability of cyclic PPA and makes it an attractive candidate for lithographic applications.

OPA | Ortho-Phthalaldehyde | Showa America | Buy OPA

Patent US6891069 - Synthesis of 4-substituted phthalaldehyde

We recently reported the cationic polymerization of o-phthalaldehyde to macrocyclic poly(phthalaldehyde) polymers. Resubjecting the cyclic polymers to the polymerization conditions led to a redistribution of the polymer to a new cyclic structure consistent with thermodynamic equilibrium. We now report the synthesis of cyclic poly(phthalaldehyde) derivatives and demonstrate the scrambling of distinct homopolymer mixtures to copolymers under the cationic polymerization conditions. Homopolymer mixtures are found to rapidly redistribute, first to multiblock cyclic copolymers. With extended reaction time, random macrocyclic copolymers are obtained. Evolution of the microstructure was monitored by NMR spectroscopy, MALDI-TOF mass spectrometry, and gel permeation chromatography (GPC). The reported scrambling method leads to the rapid preparation of macrocyclic copolymers of high molecular weight with variable microstructure depending on reaction times and catalyst loadings.

End-capped poly(phthalaldehyde) (PPA) synthesized by anionic polymerization has garnered significant interest due to its ease of synthesis and rapid depolymerization. However, alternative ionic polymerizations to produce PPA have been largely unexplored. In this report, we demonstrate that a cationic polymerization of o-phthalaldehyde initiated by boron trifluoride results in cyclic PPA in high yield, with high molecular weight, and with extremely high cyclic purity. The cyclic structure is confirmed by NMR spectroscopy, MALDI-TOF mass spectrometry, and triple-detection GPC. The cyclic polymers are reversibly opened and closed under the polymerization conditions. Owing to PPA's low ceiling temperature, cyclic PPA is capable of chain extension to larger molecular weights, controlled depolymerization to smaller molecular weights, or dynamic intermixing with other polymer chains, both cyclics and end-capped linears. These unusual properties endow the system with great flexibility in the synthesis and isolation of pure cyclic polymers of high molecular weight. Further, we speculate that the absence of end groups enhances the stability of cyclic PPA and makes it an attractive candidate for lithographic applications.

Disclosed herein are methods of synthesizing a 4-substituted-benzene-1,2-carbaldehyde
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Get supplier listing of o-Phthalaldehyde and equal product

End-capped poly(phthalaldehyde) [PPA] is a well-studied metastable polymer that has attracted interest due to its ease of synthesis and rapid depolymerization. PPA is limited, however, in the type of macromolecular architectures accessible, as functionalizable phthalaldehyde derivatives are not commercially available and their synthesis is cumbersome. To this end, a general route to phthalaldehyde-benzaldehyde copolymers was sought, as benzaldehyde comonomers with various pendant functionalities are readily available. It was found that copolymers are synthesized by an anionic initiated polymerization of phthalaldehyde and electron-deficient benzaldehydes. The comonomer reactivities are shown to be sensitive to the benzaldehyde electronics; the relative reactivity of phthalaldehyde-benzaldehyde comonomer pairs strongly correlate with the Hammett values of the benzaldehyde monomer. These copolymers are then further modified to yield cross-linked, degradable polymer networks in just a two-step sequence. Phthalaldehyde-benzaldehyde copolymers thus enable functionalization of metastable polymers that rapidly depolymerize upon exposure to acid, thereby facilitating the development of triggerable degradation of polymer networks.

Synthesis and Characterization of Hexaazamacrocyclic Complexes ..

N2 - End-capped poly(phthalaldehyde) [PPA] is a well-studied metastable polymer that has attracted interest due to its ease of synthesis and rapid depolymerization. PPA is limited, however, in the type of macromolecular architectures accessible, as functionalizable phthalaldehyde derivatives are not commercially available and their synthesis is cumbersome. To this end, a general route to phthalaldehyde-benzaldehyde copolymers was sought, as benzaldehyde comonomers with various pendant functionalities are readily available. It was found that copolymers are synthesized by an anionic initiated polymerization of phthalaldehyde and electron-deficient benzaldehydes. The comonomer reactivities are shown to be sensitive to the benzaldehyde electronics; the relative reactivity of phthalaldehyde-benzaldehyde comonomer pairs strongly correlate with the Hammett values of the benzaldehyde monomer. These copolymers are then further modified to yield cross-linked, degradable polymer networks in just a two-step sequence. Phthalaldehyde-benzaldehyde copolymers thus enable functionalization of metastable polymers that rapidly depolymerize upon exposure to acid, thereby facilitating the development of triggerable degradation of polymer networks.

Synthesis and Characterization of Hexaazamacrocyclic ..

AB - End-capped poly(phthalaldehyde) [PPA] is a well-studied metastable polymer that has attracted interest due to its ease of synthesis and rapid depolymerization. PPA is limited, however, in the type of macromolecular architectures accessible, as functionalizable phthalaldehyde derivatives are not commercially available and their synthesis is cumbersome. To this end, a general route to phthalaldehyde-benzaldehyde copolymers was sought, as benzaldehyde comonomers with various pendant functionalities are readily available. It was found that copolymers are synthesized by an anionic initiated polymerization of phthalaldehyde and electron-deficient benzaldehydes. The comonomer reactivities are shown to be sensitive to the benzaldehyde electronics; the relative reactivity of phthalaldehyde-benzaldehyde comonomer pairs strongly correlate with the Hammett values of the benzaldehyde monomer. These copolymers are then further modified to yield cross-linked, degradable polymer networks in just a two-step sequence. Phthalaldehyde-benzaldehyde copolymers thus enable functionalization of metastable polymers that rapidly depolymerize upon exposure to acid, thereby facilitating the development of triggerable degradation of polymer networks.

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