Coupling of Epoxides and Lactones by Cationic Indium Catalysts To Form Functionalized Spiro‐Orthoesters

Jung, Hyuk-Joon; Chang, Chen; Yu, Insun; Aluthge, Dinesh C.; Ebrahimi, Tannaz; Mehrkhodavandi, Parisa

doi:10.1002/cctc.201800474

Cited by 21 publications

(27 citation statements)

References 85 publications

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“… 23 In particular, we showed that cationic indium complex (±)-[(NN i O Cm )In(CH 2 SiMe 3 )][B(3,5-(CF 3 ) 2 C 6 H 3 ) 4 ] (Cm = Cumyl) catalyzes the coupling of an equimolar mixture of ε-caprolactone (ε-CL) and 1,2-epoxy-7-octene (EOE) to form 2-(hex-5-en-1-yl)-1,4,6-trioxaspiro[4.6]undecane (SOE1) in near quantitative isolated yield. 24 We showed that 5, 6, and 7-membered lactones as well as epoxides with a range of functionality are converted to the respective spiroorthoesters quantitatively. 24 …”

Section: Introductionmentioning

confidence: 89%

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Temperature triggered alternating copolymerization of epoxides and lactones via pre-sequenced spiroorthoester intermediates

2022

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Section: Introductionmentioning

confidence: 89%

“… 24 We showed that 5, 6, and 7-membered lactones as well as epoxides with a range of functionality are converted to the respective spiroorthoesters quantitatively. 24 …”

Section: Introductionmentioning

confidence: 89%

Temperature triggered alternating copolymerization of epoxides and lactones via pre-sequenced spiroorthoester intermediates

2022

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“…40 kg/mol with relatively narrow dispersity (Đ < 1.3). [49][50][51] This system also effectively copolymerized ECH with THF, oxetane, oxepane, and lactide to make some interesting copolymers.…”

Section: Cationic Ring Opening Polymerization Of Echmentioning

confidence: 99%

The versatile, functional polyether, polyepichlorohydrin: History, synthesis, and applications

Shukla

Ferrier

2021

Journal of Polymer Science

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Polyepichlorohydrin (PECH) is a functional polyether first synthesized in the 1950's by the catalytic ring opening polymerization of epichlorohydrin (ECH), its inexpensive epoxide pre-cursor. PECH elastomers are used in diverse commercial applications due to their unique combination of properties including low temperature flexibility and heat and oil resistance. PECH holds an interesting place in polymer history as its synthesis led to the discovery of highly effective aluminum-based catalysts for epoxide polymerizations and a new class of high molecular weight polyether elastomers by an exceptional polymer chemist, Edwin J. Vandenberg. ECH is an ideal feedstock for polymer materials as it is functional, inexpensive, and produced through environmentally friendly means. However, due to the alkyl chloride pendant, polymerizations involving ECH are difficult and limited synthetic advancement has occurred until very recently. This focused review will discuss modern polymerization methods involving ECH while giving a historical perspective on the evolution of these techniques. We will also review applications of ECH-based polymers and discuss the future development of these materials. We hope to convince the reader to explore ECH-based materials in their own work.

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“…Mehrkhodavandi et al prepared a cationic indium-based catalyst for the synthesis of SOEs from lactones and epoxides [ 63 ]. The indium complex catalyzes the reaction of 1:1 mixtures of a variety of epoxides and lactones into SOEs, which were obtained as racemic mixtures of diastereomers.…”

Section: Expanding Oxacyclesmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

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Coupling of Epoxides and Lactones by Cationic Indium Catalysts To Form Functionalized Spiro‐Orthoesters

Cited by 21 publications

References 85 publications

Temperature triggered alternating copolymerization of epoxides and lactones via pre-sequenced spiroorthoester intermediates

Temperature triggered alternating copolymerization of epoxides and lactones via pre-sequenced spiroorthoester intermediates

The versatile, functional polyether, polyepichlorohydrin: History, synthesis, and applications

Expanding Monomers as Anti-Shrinkage Additives

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