Novel ring-expansion reaction between cyclic formal and ethylene oxide

Yamasaki, Naoaki; Nagahara, Hajime; Masamoto, Junzo

doi:10.1016/s0040-4039(00)01870-0

Cited by 20 publications

(6 citation statements)

References 4 publications

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“…However, there is a newly discovered mechanism for the copolymerization of trioxane and ethylene oxide: several new intermediates are found, including 1,3,7‐tetraoxacyclononane (TOCN), 1,3,5,7,10‐pentaoxacyclododecane (POCD), and 1,3,5,7,10,13‐hexaoxacycloheptadecane (HOCP), which are the products from the direct reaction of trioxane and ethylene oxide 17, 18. All these intermediates transfer to 1,3‐dioxolane and TOXP in the latter period of the polymerization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and crystallization behavior of acetal copolymer/silica nanocomposite by in situ cationic ring‐opening copolymerization of trioxane and 1,3‐dioxolane

Sun

Yang

2007

J of Applied Polymer Sci

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ABSTRACT:The acetal copolymer/silica nanocomposite was prepared by in situ bulk cationic copolymerization of trioxane and 1,3-dioxolane in the presence of nanosilica. The crystallization behavior of acetal copolymer/silica nanocomposite was studied by AFM, DSC, XRD, and CPOM, and the macromolecular structure of acetal copolymer/silica nanocomposite was characterized by FTIR and 1 H-NMR. The 1 H-NMR results showed that the macromolecular chain of acetal copolymer had more than two consecutive 1,3-dioxolane units in an oxymethylene main chain, while that of acetal copolymer/silica nanocomposite had only one 1,3-dioxolane unit in an oxymethylene main chain. There existed interaction between the macromolecular chains and nanoparticles (such as hydrogen bonds and coordination). On one hand, nanoparticles acted as nucleation center, which accelerated the crystallization rate but reduced the crystallinity. The spherulite sizes also decreased with addition of nanoparticles attributed to the nucleation effect. On the other hand, the presence of nanoparticles interrupted the spherical symmetry of the crystallite. In conclusion, the high surface energy and small scale of nanoparticles have a prominent impact on the polymerization mechanism and crystallization behavior of nanocomposite.

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Section: Introductionmentioning

confidence: 99%

Synthesis and crystallization behavior of acetal copolymer/silica nanocomposite by in situ cationic ring‐opening copolymerization of trioxane and 1,3‐dioxolane

Sun

Yang

2007

J of Applied Polymer Sci

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“…Formation of diethylene glycol formal (1,3,6-trioxacyclooctane -TCO) was observed upon the reaction of 1,3-dioxolane (DXL) with ethylene oxide (EO). 14 With 1 mol% of EO with respect to DXL $80% of diethylene glycol formal (with respect to EO) was observed after 20 min. of reaction with BF 3 Bu 2 O as catalyst at 30 C. A small amount ($10% with respect to EO) of triethylene glycol formal was also found.…”

Section: Synthesis Of Higher Cyclic Formalsmentioning

confidence: 97%

Synthesis and polymerization of cyclic formals of oligooxyethylene diols

Kubisa

2023

Polymers for Advanced Techs

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Polymers of general formula [−(CH2CH2O)m‐CH2O‐]n with well‐defined m value may be obtained by cationic ring‐opening polymerization of easily available cyclic formals of di‐, tri‐, tetra‐, penta‐ (and possibly higher) ethylene glycols. There are no significant kinetic or thermodynamic restrictions for their polymerization. Polymers with [(‐CH2CH2O)m‐CH2O‐]n structure may be treated as intermediates between polymers of ethylene oxide (POE) and polymers of 1,3‐dioxolane (PDXL), both of which find applications in the biomedical field as well as components of solid polymer electrolytes. Largely unexploited [(‐CH2CH2O)m‐CH2O‐]n polymers may broaden the scope of the application of polyacetals in both these areas.

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“…Condensation of resorcinol with aldehydes forms calix [4]resorcinarenes, but only one member of the family is known (Scheme 29) [78], although a calix [5]arene with resorcinol connected in a different position is also known [79]. It is most likely that resorcinarenes of other ring sizes can be produced in a manner similar to that used for the syntheses in the calixarene family.…”

Section: Macrocyclic Compounds Formed By Six New Bondsmentioning

confidence: 99%

“…Up to now, cryptands, biscrown ethers, supercryptands, cylindrical polycyclic compounds and cubic compounds have been prepared by direct one-step methods. However, nearly every day additional new and unique structures are added to this list [3,4].…”

Section: Introductionmentioning

confidence: 99%

One‐step syntheses of macrocyclic compounds: A short review

Krakowiak

Izatt

Bradshaw

2001

Journal of Heterocyclic Chem

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Macrocyclic ligands have been prepared by various one-step cyclooligomerization processes. This short review covers one-step cyclization reactions involving the formation of four to twenty or more new covalent bonds. The new macrocycles reviewed include cyclophanes, biscrown ethers, cryptands, macrolides, cage compounds, calixarenes, homocalixarenes, cucubiturils, and supercryptands all prepared by one-step syntheses.

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Novel ring-expansion reaction between cyclic formal and ethylene oxide

Cited by 20 publications

References 4 publications

Synthesis and crystallization behavior of acetal copolymer/silica nanocomposite by in situ cationic ring‐opening copolymerization of trioxane and 1,3‐dioxolane

Synthesis and crystallization behavior of acetal copolymer/silica nanocomposite by in situ cationic ring‐opening copolymerization of trioxane and 1,3‐dioxolane

Synthesis and polymerization of cyclic formals of oligooxyethylene diols

One‐step syntheses of macrocyclic compounds: A short review

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