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  • Polymer and Materials Science  (9)
  • Allylic rearrangement  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and properties of polyurethanes derived from diaminodianhydroalditols (1986)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 187 (1986), S. 2775-2785 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The readily accessible 1,4:3,6-dianhydroalditols with D-gluco- (1), L-ido- (5) and D-mannoconfigurations (6) were efficiently transformed into the 2,5-diamino-1,4:3,6-dianhydro-2,5-dideoxyalditols with D-gluco- (10), D-manno- (13), and L-ido-configuration (16). Interfacial polycondensation of these chiral heterocyclic diamines as well as ethylene- and tetramethylene diamine with the bis(chloroformate) 3 derived from 1,4:3,6-dianhydro-D-sorbitol gave the polyurethanes 17 to 21. Their number-average molecular weights were determined to be M̄n ≈ 3000 corresponding to an average degree of polymerisation P̄n ≈ 20. Inherent viscosities were measured, and 1H NMR spectroscopy as well as DSC gave informations about the molecular structure and some polymer properties.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1986.021871204
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  • 2
    Electronic Resource
    Electronic Resource
    Syntheses and properties of polyamides from glucosamine and glucose derivatives (1993)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 194 (1993), S. 1035-1057 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Starting from D-glucosamine, the synthesis of various differently modified methyl and benzyl 2,6-diaminosaccharides 11, 12, 17 and 18 was accomplished. Interfacial and solution polycondensation of those diamino derivates with aromatic and aliphatic acyl chlorides yielded polyamides 34, 35, 36 and 37a-d which were characterized by 1H NMR spectroscopy and their inherent viscosities. The presence of an anomeric benzyl group in 12 did not decrease the reactivity of the 2-amino function. The free hydroxy functions in polyamides 35a-b were acetylated to give polyamides 39a-b. Partially blocked polyamides 36a-d had similar properties as unprotected polyamides 34-35a-d. Under corresponding conditions di-O-acylated diaminosaccharide 18 gave only oligomer. Number-average molecular weights were obtained from gel-permeation chromatography to be 10300 〈 M̄n 〈 24000 (interfacial polycondensation), corresponding to number-average degrees of polymerization up to P̄n = 64, whereas polycondensation in solution afforded only M̄n values between 2000 and 3000. Starting with D-glucose the synthesis of a C-glycosidic diaminosaccharide 28 was developed. This reacted to polyamides 38a-d which showed thermal stability up to 280°C.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1993.021940401
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  • 3
    Electronic Resource
    Electronic Resource
    Ring-opening polymerization of cis-3,4-dimethoxyoxolane (1987)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 188 (1987), S. 711-718 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The reaction conditions for the ring-opening polymerization of cis-3,4-dimethoxyoxolane (1,4-anhydro-2,3-di-O-methyl-D-erythritol, 3) using fluorosulfonic acid as initiator are described. The resulting polyether 4, poly[oxy(2,3-dimethoxytetramethylene)], is characterized by elucidation of M̄n and M̄w, elemental analysis, 1H NMR spectroscopy as well as terminal group determination. The optimum conditions for obtaining high molecular weight polymers 4 are established and discussed.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1987.021880405
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  • 4
    Electronic Resource
    Electronic Resource
    Ring-opening polymerization of carbohydrate-derived dialkoxyoxolanes. Approaches to functionalized poly(oxytetramethylene)s (1989)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 190 (1989), S. 1737-1753 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: A series of various cis-3,4-diacyloxy- and dialkyloxy-oxolanes (4 to 14) as well as the oxolanes 16 and 17 were prepared. Ring-opening polymerizations of the dialkyloxy derivatives 4, 6, and 11 using the super-acids FSO3H and CF3SO3H led to novel functionalized poly[oxy(2,3-dialkyloxy-tetramethylene)]s. The reaction parameters were thoroughly studied, and optimum conditions lead to a DPn up to 35. All polyethers were fully assigned by polymer analytical procedures such as GPC, osmometry, 1H NMR spectroscopy and end group determination. In the case of the mixed benzyloxy methyloxy polymer 22, by subsequent hydrogenolysis a component with hydroxy functions was obtained. This procedure features a novel change of functionality in selectively derivatized polyethers originally derived from regrowing carbohydrate material.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1989.021900801
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis and ring-opening polymerization of 1,4:2,5:3,6-trianhydro-D-mannitol and structure studies by MNDO calculations (1991)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 192 (1991), S. 317-331 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Base-catalyzed intramolecular nucleophilic substitution of various dianhydrosorbitol derivatives (2, 4, or 6) led to formation of trianhydromannitol (7), a tricyclic system of three interlinked oxolane rings. By treatment with trifluoromethanesulfonic acid, ring-opening reactions were achieved to give oligomeric soluble material with a number-average degree of polymerization \documentclass{article}\pagestyle{empty}\begin{document}$ \overline {DP} _n \approx 5 - 10 $\end{document} Molecular weights were determined by GPC, and by desorptive chemical ionization (DCI) with ammonia a molecular weight assignment gave information on the degree of crosslinking. A complex but consistent picture allows to explain the propagation reactions of protonated trianhydromannitols 8 and 9, and further reactions of the protonated intermediates 13-15 to result in crosslinked products 16 and 17. By semiempirical quantum chemical calculations, geometries, energies and charge distributions of 7 as well as its protonated species were obtained. This allowed comparisons with their chemical reactivity and ring-opening specificity.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1991.021920214
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis and properties of polyamides derived from anhydro- and dianhydroalditols (1991)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 192 (1991), S. 2163-2182 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The three isomeric 1,4:3,6-dianhydroalditols with D-gluco- (2), D-manno- (11) and L-ido (17) configuration and both 1,4-anhydroalditols with threo (22) and erythro (27) configuration were efficiently transformed into the corresponding diamino derivatives. Interfacial polycondensation of these chiral heterocyclic diamines with purchasable aromatic and aliphatic carboxylic acid chlorides gave polyamides 35 and 36a-f, 37, 38 and 39a-d. The polymers were characterized using IR and 1H/13C NMR spectroscopy. Number-average molecular weights were obtained from gel-permeation chromatography to be M̄n ≈ 5000-25000 corresponding to a number-average degree of polymerization up to P̄n ≈ 100. Inherent viscosities were measured, and differential scanning calorimetry gave information on the thermal properties of the polymers.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1991.021920922
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of hydrophilic carbohydrate-derived polyamides (1992)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 30 (1992), S. 2059-2062 
    Details
    ISSN: 0887-624X
    Keywords: polyamides ; interfacial polycondensation ; anhydro saccharides ; galactaric acid ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1992.080300934
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  • 8
    Electronic Resource
    Electronic Resource
    Ring-opening copolymerization of anhydroalditols with tetrahydrofuranDedicated to the 65th anniversary of Prof. Dr. Dr. E. H. Hansjörg Sinn (1995)
    Weinheim : Wiley-Blackwell
    Macromolecular Chemistry and Physics 196 (1995), S. 1487-1493 
    Details
    ISSN: 1022-1352
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: By ring-opening copolymerization of 1,4-anhydro-2,3-di-O-ethyl-D-erythritol (cis-3,4-diethoxyoxolane, 1) or 1,4:2,5:3,6-trianhydro-D-mannitol (3) with tetrahydrofuran carbohydratecontaining copolyether polyols were obtained. Using trifluoromethanesulfonic acid as catalyst the molecular weights were in a range from M̄w = 13 000 up to 25 000 with about 10% of carbohydrate constituent. The novel copolyethers were studied by polymer analytical procedures, their structures4 and 5 tentatively assigned and compared to the homopolymerization products of the monomers. The present procedure features an approach to novel partially functionalized high molecular weight copolymer polyols based on carbohydrate-derived materials.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1995.021960511
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis of a novel starch-derived AB-type polyurethane (1998)
    Weinheim : Wiley-Blackwell
    Macromolecular Rapid Communications 19 (1998), S. 21-26 
    Details
    ISSN: 1022-1336
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Starting from 1,4:3,6-dianhydrosorbitol (DAS, 1), a five step monomer synthesis led to 2-deoxy-1,4:3,6-dianhydro-2-isocyanato-L-iditol, 9, which by catalytic polyaddition gave polyurethane 13. A second route required the synthesis of 2-azido-5-O-chloroformyl-2-deoxy-1,4:3,6-dianhydro-L-iditol, 11. During catalytic hydrogenation, the intermediate 2-aminochloroformyl derivative 12 underwent spontaneous polycondensation. The structure of 13 was characterized by 1H and 13C NMR, IR spectroscopy and elemental analyses. Gel-permeation chromatography showed M̄n = 8 000-12 000 corresponding to a degree of polymerisation up to 70. Differential scanning calorimetry revealed the polyadduct to be semicrystalline with a glass transition at Tg = 118°C and a melting range of 190-200°C. The polycondensation product was found to be crystalline with a melting range of 140-180°C.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Artificial deoxy glycosides of anthracyclines (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 509-512 
    Details
    ISSN: 0170-2041
    Keywords: Anthracycline glycosides ; Allylic rearrangement ; Glycosylation ; NIS procedure ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In Lewis acid mediated allylic rearrangement reactions of L-rhamnal (1) and L-fucal (2) with daunomycinon (6) 2′-deoxyhex-2′-enopyranosides have been obtained exclusively. Furthermore, glycals 1 and 4 have been treated with the glycosyl acceptors 6, 7, and 9 and N-iodosuccinimide (NIS) to produce the corresponding α-configurated 2′-deoxy-2′-iodo glycosides. Among these, 16 represents a bis (glycoside) with both benzylic aglycon positions substituted. In none of the above cases has a substantial amount of β-glycoside been detected. Attempts to convert ε-isorhodomycinon (8) into a glycoside on a preparative scale, under Lewis acid conditions have been unsuccessful. However, the α-glycoside 13 has been obtained by the Helferich method.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910193
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