New evidences of the degradation mechanism of poly(oxy-1-chloromethylethylene) with basic reagents: studies with poly(oxy-1-chloromethyl-ethylene- co -oxyethylene)

Pérez, Mónica; Reina, José Antonio; Serra, Àngels; Ronda, Juan C.

doi:10.1016/s0032-3861(00)00081-1

Cited by 15 publications

(6 citation statements)

References 9 publications

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“…The major drawback of the nucleophilic displacement of the PECH chlorine atom is the dehydrochlorination side reaction and the fact that the resulting vinylether units degrade the polymer 31, 38, 39. These competitive reactions related to the basicity of the nucleophile seem to play a significant role for phenolates but are negligible in aromatic carboxylates, as can be seen here.…”

Section: Resultsmentioning

confidence: 55%

Gold‐Catalyzed Intermolecular Addition of Carbonyl Compounds to 1,6‐Enynes: Reactivity, Scope, and Mechanistic Aspects

Schelwies

Moser

Dempwolff

et al. 2009

Chemistry A European J

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A full account of a recently discovered gold(I)-catalyzed reaction, a cycloaddition of carbonyl compounds to enynes yielding 2-oxabicyclo[3.1.0]hexanes with four stereogenic centers, is presented. The reaction proceeds with very high diastereoselectivity. The scope of the reaction has been investigated. In addition, experiments and DFT calculations concerning mechanistic aspects were carried out. The reaction course varies with the substitution pattern of the alkene moiety of the starting enyne. Branched olefins led to 2-oxabicyclo[3.1.0]hexanes; terminally substituted olefins proceeded with the incorporation of two carbonyl components to give hexahydrocyclopenta[d][1,3]dioxines.

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Section: Resultsmentioning

confidence: 55%

Gold‐Catalyzed Intermolecular Addition of Carbonyl Compounds to 1,6‐Enynes: Reactivity, Scope, and Mechanistic Aspects

Schelwies

Moser

Dempwolff

et al. 2009

Chemistry A European J

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“…The chemical modification of PECH under phase‐transfer catalyst conditions with carboxylates has been used by several researchers,26, 27 but very few studies have focused on obtaining anisotropic materials 28, 29. The fact that the modification degrees in our previous article were good and that no dehydrochlorination30, 31 side reactions were detected encouraged us to use the same strategy and reaction conditions here.…”

Section: Resultsmentioning

confidence: 94%

Self‐organized liquid‐crystalline polyethers obtained by grafting tapered mesogenic groups onto poly(epichlorohydrin): Toward biomimetic ion channels 2

Ronda

Reina

Giamberini

2003

J. Polym. Sci. A Polym. Chem.

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A set of high‐molecular‐weight, new, side‐chain liquid‐crystalline polyethers was obtained by chemical modification of poly(epichlorohydrin) with potassium 3,4,5‐tris[4‐(n‐dodecan‐1‐yloxy)benzyloxy]benzoate. The degree of modification depended on the reaction conditions and ranged from 39 to 58%. The highest value was an apparent modification plateau. NMR characterization indicated no side reactions of any kind (e.g., deshydrohalogenation). All random‐grafted copolymers had hexagonal columnar mesophases with the exception of the least modified copolymer, which had a nematic columnar mesophase. X‐ray diffraction experiments performed on mechanically oriented samples showed that tapered groups were tilted with respect to the column axes. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 326–340, 2004

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“…The materials obtained have shown good liquid crystalline behavior, but modification degrees have been relatively high only when the samples were of low molecular weight. Moreover, chemically modifying the chloromethyl pendant group with basic reagents leads to partial dehydrochlorination and chain‐cleavage side processes,14, 15 which in turn lead to undesired polymer units. The polymerization route has also been considered by several authors.…”

Section: Introductionmentioning

confidence: 99%

Studies on the modification of poly(ω‐bromoalkyl‐1‐glycidylether)s with 4′‐methoxybiphenyl‐4‐oxy mesogenic groups

Montornés¹,

Reina²,

Ronda³

2005

J. Polym. Sci. A Polym. Chem.

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A series of poly[ω‐(4′‐methoxy‐biphenyl‐4‐oxy)alkyl‐1‐glycidylether]s were synthesized by chemically modifying the corresponding poly(ω‐bromoalkyl‐1‐glycidylether)s with the sodium salt of 4‐hydroxy‐4′‐methoxybiphenyl. New high‐molecular‐weight side‐chain liquid‐crystalline polymers were obtained with excellent yields and almost quantitative degrees of modification. They were all insoluble in THF and other common solvents. Characterization by 13C NMR confirmed that all the polymers had the expected structure. The liquid crystalline behavior of the polymers was analyzed by DSC and polarized optical microscopy, and mesophase assignments were confirmed by X‐ray diffraction studies. Polymers that had alkyl spacers with n = 2 and 4 were smectic C, those that had spacers with n = 6 and 8 were nematic cybotactic, and those that had longer spacers (n = 10 and 12) were smectic C again. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5998–6006, 2005

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New evidences of the degradation mechanism of poly(oxy-1-chloromethylethylene) with basic reagents: studies with poly(oxy-1-chloromethyl-ethylene- co -oxyethylene)

Cited by 15 publications

References 9 publications

Gold‐Catalyzed Intermolecular Addition of Carbonyl Compounds to 1,6‐Enynes: Reactivity, Scope, and Mechanistic Aspects

Gold‐Catalyzed Intermolecular Addition of Carbonyl Compounds to 1,6‐Enynes: Reactivity, Scope, and Mechanistic Aspects

Self‐organized liquid‐crystalline polyethers obtained by grafting tapered mesogenic groups onto poly(epichlorohydrin): Toward biomimetic ion channels 2

Studies on the modification of poly(ω‐bromoalkyl‐1‐glycidylether)s with 4′‐methoxybiphenyl‐4‐oxy mesogenic groups

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