A Short and Simple Synthesis of Ketene Acetals

Argade, A. B.; Joglekar, Bharati

doi:10.1080/00397919308009857

Cited by 10 publications

(9 citation statements)

References 17 publications

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“…The products were eluted from a silica gel column with ethyl acetate−hexane (1:5). The products were identified by their MS, elemental analyses, and NMR spectra compared with known ketene acetals. , …”

Section: Methodsmentioning

confidence: 99%

Organometallic Catalysis: Formation of 1,3-Dioxolanes and Their Analogs Catalyzed by Methylrhenium Trioxide (MTO)

Zhu

Espenson

1997

Organometallics

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Methylrhenium trioxide (MTO) catalyzes several cycloaddition reactions. 1,3-Dioxolanes were obtained in good yields from the reactions of epoxides with aldehydes or ketones; the geometric configuration of the epoxide substituents remains unchanged in the product, which was shown to be the consequence of two configuration inversions in sequence. The independently known bis(alkoxy)rhenium complex formed from MTO and the epoxide is an intermediate that could be detected at a low level during the reaction; indeed, its formation limits the rate of the overall reaction. Related cycloaddition reactions are the formation of ketene acetals from diphenylketene and epoxides and of oxazolidines from aromatic imines and epoxides, both MTO-catalyzed.

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Section: Methodsmentioning

confidence: 99%

Organometallic Catalysis: Formation of 1,3-Dioxolanes and Their Analogs Catalyzed by Methylrhenium Trioxide (MTO)

Zhu

Espenson

1997

Organometallics

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“…[162][163] More recently, a new route for 5-membered CKA was proposed from acetonitrile and ethylene glycol. 164 The reaction took several days to proceed but did not require any intermediate purification step (Figure 62). 164 In 1995, Petasis 165 described an enhanced process of Tebbe's olefination 166 and used it to modify several carbonyl functions.…”

Section: Figure 61 Synthesis Of Ketene Acetals As Described By MCmentioning

confidence: 99%

“…164 The reaction took several days to proceed but did not require any intermediate purification step (Figure 62). 164 In 1995, Petasis 165 described an enhanced process of Tebbe's olefination 166 and used it to modify several carbonyl functions. He proved for example that by using dimethyltitanocene and cyclic carbonate, it was possible to obtain CKA in small quantity but with very good yields (Figure 63).…”

Section: Figure 61 Synthesis Of Ketene Acetals As Described By MCmentioning

confidence: 99%

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Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

et al. 2017

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Cyclic monomers bearing either vinyl or exomethylene groups have the ability to be polymerized through a radical pathway via a ring-opening mechanism (addition-fragmentation process), leading to the introduction of functionalities in the polymer backbone. Radical ring-opening polymerization (rROP) combines the advantages of both ring-opening polymerization and radical polymerization, that is the preparation of polymers bearing heteroatoms in the backbone but with the ease and robustness of a radical process. This current review presents a comprehensive description of rROP by detailing: (i) the various monomers that polymerize through rROP; (ii) the main parameters that govern the rROP mechanism; (iii) the copolymerization by conventional or controlled/living radical polymerization between rROP monomers and traditional vinyl monomers to obtain copolymers with advanced properties; (iv) the different applications (low shrinkage materials and preparation of (bio)degradable materials) of rROP monomer-containing materials, and (v) the main alternatives to rROP to induce degradability to materials obtained by a radical polymerization.

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“…On the downside, the formation of the intermediate salt took several days, but this was counterbalanced by the upside that no intermediate purification step was required. [ 54 ]…”

Section: Cka Monomer Synthesismentioning

confidence: 99%

Current Standing on Radical Ring‐Opening Polymerizations of Cyclic Ketene Acetals as Homopolymers and Copolymers with one another

Deng

Mehner

Gaitzsch

2023

Macromol. Rapid Commun.

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Radical Ring‐opening polymerization (RROP) of cyclic ketene acetals (CKAs) emerges to be a valuable polymerization technique. In attracting more attention, RROP has seen a new spike in publications, which the authors will put into perspective. This review will hence address the progress made on the number of available CKAs and the synthetic strategies to get them. In grouping, the available monomers into distinct categories, the enormous variety of available CKAs will be highlighted. Polymerizations of CKAs without vinylenes have the potential to yield fully biodegradable polymers, which is why this kind of polymerization is the focus of this review. Detailing the current understanding of the mechanism, the various side reactions will be noted and also their effect on the overall properties of the final polymers. Current attempts to control the ring‐retaining and branching reactions will be discussed as well. In addition to the polymerization itself, the available materials will be discussed as well as homopolymers, copolymers of CKAs, and block‐copolymers with pure CKA‐blocks have significantly widened the range of possible applications of materials from RROP. Altogether this review highlights the progress in the entire field of RROP just of CKAs to give a holistic overview of the field.

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A Short and Simple Synthesis of Ketene Acetals

Cited by 10 publications

References 17 publications

Organometallic Catalysis: Formation of 1,3-Dioxolanes and Their Analogs Catalyzed by Methylrhenium Trioxide (MTO)

Organometallic Catalysis: Formation of 1,3-Dioxolanes and Their Analogs Catalyzed by Methylrhenium Trioxide (MTO)

Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials

Current Standing on Radical Ring‐Opening Polymerizations of Cyclic Ketene Acetals as Homopolymers and Copolymers with one another

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