Relative reactivities of cyclic ketene acetals via cationic 1,2-vinyl addition copolymerization1

Cao, Liwei; Wu, Zhihong; Pittman, Charles U.

doi:10.1002/(sici)1099-0518(19990801)37:15<2841::aid-pola18>3.0.co;2-n

Cited by 10 publications

(8 citation statements)

References 24 publications

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“…MBL is known to get polymerized via anionic polymerization [7] and MDO by cationic polymerization [25,26] to give both ring-opening and ring-retaining polymerization, though ring-retaining is the more preferred one. The possibilities of formation of homopolymers can be ruled out easily because the glass transition temperature of the obtained polymers matched with neither of the homopolymers (A-D: Scheme).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of High‐Molecular‐Weight Tulipalin‐A‐Based Polymers by Simple Mixing and Heating of Comonomers

Agarwal

Kumar

2011

Macro Chemistry & Physics

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The preparation of a polymer based on Tulipalin A with degradable ester linkages and high glass transition temperature with good processability, and solubility in various organic solvents is reported. The reaction was performed by mixing Tulipalin A and 2‐methylene‐1,3‐dioxepane (MDO) at high temperatures (70 °C and above) in the entire composition range without any initiator. The polymerization mechanism is found to be different from mere thermal initiation at high temperature. It was a combination of ionic and radical mechanism as proved by different methods. Microstructure analysis was done by 1D and 2D NMR techniques. The reactions were also tuned for different structures with varied properties by adding either the radical trapping agent or radical generators in the system. magnified image

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Section: Resultsmentioning

confidence: 99%

Synthesis of High‐Molecular‐Weight Tulipalin‐A‐Based Polymers by Simple Mixing and Heating of Comonomers

Agarwal

Kumar

2011

Macro Chemistry & Physics

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“…Different initiating acidic systems have been tested such as methanesulfonic acid, trifluoromethanesulfonic acid 173 and H 2 SO 4 on glass balls 174 or carbon black. [175][176][177][178] The polymerizations were performed in a few hours, either at room temperature or at 60 °C. Others cationic initiating systems prepared in solution (e.g., BF 3 .Et 2 O, NiCl 2 , ZnCl 2 , FeCl 3 , AlCl 3 , ionexchange resins) usually give unstable polyacetals with unwanted polyketones or other complex side products (which colored in brown-red the reaction medium) (Figure 69).…”

Section: Cationic Polymerizationmentioning

confidence: 99%

Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

et al. 2017

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Cyclic monomers bearing either vinyl or exomethylene groups have the ability to be polymerized through a radical pathway via a ring-opening mechanism (addition-fragmentation process), leading to the introduction of functionalities in the polymer backbone. Radical ring-opening polymerization (rROP) combines the advantages of both ring-opening polymerization and radical polymerization, that is the preparation of polymers bearing heteroatoms in the backbone but with the ease and robustness of a radical process. This current review presents a comprehensive description of rROP by detailing: (i) the various monomers that polymerize through rROP; (ii) the main parameters that govern the rROP mechanism; (iii) the copolymerization by conventional or controlled/living radical polymerization between rROP monomers and traditional vinyl monomers to obtain copolymers with advanced properties; (iv) the different applications (low shrinkage materials and preparation of (bio)degradable materials) of rROP monomer-containing materials, and (v) the main alternatives to rROP to induce degradability to materials obtained by a radical polymerization.

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“…Pittman and coworkers have extensively explored the synthetic potential of many cyclic ketene acetal species [1,2] with both mono-and dielectrophiles, discovering a rich variety of reactions ranging from tandem cyclizations [1,3,4], bis additions followed by ring-opening and re-closure isomerizations [2], arylvinyl ester formation [1,4,5], ''push-pull'' compound formation [6,7], new heterocyclic ring and fused ring formation [2,3,6,8,9], ring-opening reactions [10], ring-retained polymerization and copolymerizations [11][12][13][14][15][16][17][18][19][20], spirobicyclic ring formation [21], and stereoselective radical cyclizations [21,22]. However, all of these studies have been carried out only on five-; six-; and seven-membered ring systems .…”

Section: Introductionmentioning

confidence: 99%

Four-membered ring cyclic ketene –O,O–, –O,S–, –O,N–, –S,S–, –S,N–, and –N,N–acetals and their corresponding cations: a computational study

et al. 2011

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Relative reactivities of cyclic ketene acetals via cationic 1,2-vinyl addition copolymerization1

Cited by 10 publications

References 24 publications

Synthesis of High‐Molecular‐Weight Tulipalin‐A‐Based Polymers by Simple Mixing and Heating of Comonomers

Synthesis of High‐Molecular‐Weight Tulipalin‐A‐Based Polymers by Simple Mixing and Heating of Comonomers

Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

Four-membered ring cyclic ketene –O,O–, –O,S–, –O,N–, –S,S–, –S,N–, and –N,N–acetals and their corresponding cations: a computational study

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