The Stereochemistry and Mechanism of Reversible Polymerization of 2,2-Disubstituted 1,3-Propanediol Carbonates

Sarel, Shalom; Pohoryles, Leo A.

doi:10.1021/ja01550a044

Cited by 97 publications

(69 citation statements)

References 1 publication

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“…DTC and TMC were synthesized according to a known method [5] and dried over P 2 O 5 before use. CL (Mitsubishi Chemical) was distilled under reduced pressure.…”

Section: Experimental Partmentioning

confidence: 99%

Lanthanum Tris(2,6-di-tert-butyl-4-methylphenolate) as a Novel, Versatile Initiator for Homo- and Copolymerization of Cyclic Carbonates and Lactones

Ling

2002

Macromol. Chem. Phys.

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“…DTC and TMC were synthesized according to a known method [5] and dried over P 2 O 5 before use. CL (Mitsubishi Chemical) was distilled under reduced pressure.…”

Section: Experimental Partmentioning

confidence: 99%

Lanthanum Tris(2,6-di-tert-butyl-4-methylphenolate) as a Novel, Versatile Initiator for Homo- and Copolymerization of Cyclic Carbonates and Lactones

Ling

2002

Macromol. Chem. Phys.

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“…Depolymerisations proved to be a convenient method for the preparation of new cyclic compounds that are inaccessible by classical routes. The first to use ring-closing depolymerisation for the synthesis of cyclic monomers were Sarel and Pohoryles [2] who synthesized 2,2-dimethyltrimethylene carbonate by ring-closing depolymerisation of the polycarbonate obtained from 2,2-dimethylpropane-1,3-diol and diethyl carbonate in the presence of potassium carbonate as a catalyst. Later this procedure was further developed by co-workers of Bayer AG who prepared a series of 2,2-disubstituted trimethylene carbonates (six-membered cyclic carbonates) but also higher-membered cyclic carbonates.…”

Section: Introductionmentioning

confidence: 99%

Interconversion of Alternating Poly(ester amide)s and Cyclic Ester Amides from Adipic Anhydride and α,ω‐Amino Alcohols

Fey

Keul

Höcker

2003

Macro Chemistry & Physics

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Poly(esters amide)s from adipic anhydride and α,ω‐amino alcohols were obtained by polycondensation of α‐carboxyl‐ω‐hydroxyl amides under mild conditions in solution or by bulk polycondensation at elevated temperatures. For the polycondensation in bulk the influence of catalyst and of temperature on the number‐average molecular weight was studied. At a temperature of 170 °C the polycondensation process is followed by a ring‐closing depolymerisation and the formation of cyclic ester amides. Ten‐ to fourteen‐membered cyclic ester amides were obtained and characterized. The ring‐opening polymerisation of these cyclic ester amides leads, in a controlled mode, to poly(ester amide)s. The interconversion of poly(ester amide)s and cyclic ester amides by ring‐closing depolymerisation and ring‐opening polymerisation is possible. The poly(ester amide)s from adipic anhydride and homologous α,ω‐amino alcohols H2N(CH2)xOH (x = 2–6) are semicrystalline materials, their melting points show the odd/even effect observed for [n]‐polyamides and [n]‐polyurethanes.

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“…It has been known that the polycarbonate 3d is depolymerized by heating to afford the cyclic carbonate 9d. 19 So, the decrease in the polymer yield is reasonably explained by the depolymerization of 3d-type sequence formed in the early stage of the polymerization (eq 7). The carbonate 9d was isolated by sublimation from the polymerization mixture in vacuo.…”

Section: Bmentioning

confidence: 87%

Effect of Substituents on Cationic Polymerization of Six-Membered Spiro Orthocarbonates

Fujinami

Tsuji

Sakai

1977

Polym J

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ABSTRACT:Six-membered spiro orthocarbonates with methyl substituents were prepared from cyclic dibutylstannyl glycolates and carbon disulfide, then polymerized using boron trifluoride etherate as the catalyst in l,2-dichloroethane at 30°C. The methyl substituent caused a decrease in the polymer yield. The 2,8-dimethyl and 2,4,8,10-tetramethyl spiro monomers were polymerized by a l,10-transfer reaction to bring about polyethercarbonates analogously to the unsubstituted spiro monomer. The spiro-monomer having 3,3,9,9-tetramethyl substituents underwent a 1,10-transfer polymerization at 30°C accompanied with the formation of polycarbonate segment which was partially depolymerized to the corresponding cyclic carbonate monomer at refluxing temperature of 1,2-dichloroethane. Contrary to the above, no polymer was obtained from the 2,2,4,8,8,10-hexamethyl spiro monomer.KEY WORDS Spiro Orthocarbonate / Cationic Polymerization / Transfer Polymerization / Substituent Effect / Polyethercarbonate /

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The Stereochemistry and Mechanism of Reversible Polymerization of 2,2-Disubstituted 1,3-Propanediol Carbonates

Cited by 97 publications

References 1 publication

Lanthanum Tris(2,6-di-tert-butyl-4-methylphenolate) as a Novel, Versatile Initiator for Homo- and Copolymerization of Cyclic Carbonates and Lactones

Lanthanum Tris(2,6-di-tert-butyl-4-methylphenolate) as a Novel, Versatile Initiator for Homo- and Copolymerization of Cyclic Carbonates and Lactones

Interconversion of Alternating Poly(ester amide)s and Cyclic Ester Amides from Adipic Anhydride and α,ω‐Amino Alcohols

Effect of Substituents on Cationic Polymerization of Six-Membered Spiro Orthocarbonates

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