Simple one-step preparations of vinylic carbonates from aldehydes

Olofson, R. A.; Anh, Dang Vu; Morrison, David S.; Cusati, P. F. De

doi:10.1021/jo00288a001

Cited by 18 publications

(8 citation statements)

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“…c The alkylation conversion (Conv.%) and selectivity (Sel.%) were determined with respect to reacted acylfluoride and isolated HFEs compared to the initial and reacted acylfluoride, respectively. Path (b) is also supported by literature data where fluoroformate 2 acts as acylating reagent, in particular enolizable hydrogenated alkoxy and enol aldehydes are converted to the corresponding carbonates by treatment with hydrogenated chloro-or fluoro-formates by nucleophilic attack to the carbonyl group -COF [24].…”

Section: Reaction Mechanismssupporting

confidence: 67%

New catalytic alkylation of in situ generated perfluoro-alkyloxy-anions and perfluoro-carbanions

Galimberti

Fontana

Resnati

et al. 2005

Journal of Fluorine Chemistry

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Section: Reaction Mechanismssupporting

confidence: 67%

New catalytic alkylation of in situ generated perfluoro-alkyloxy-anions and perfluoro-carbanions

Galimberti

Fontana

Resnati

et al. 2005

Journal of Fluorine Chemistry

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“…In a similar way, acetaldehyde can be converted to vinyl carbonates by treatment with chloro-or fluoroformates, KF, and a 18-crown-6 ether or by reaction of fluoroformates on KF in DMSO without any further catalyst in 56-92% yield (Scheme 1d). 26 For industrial scale synthesis, a patent for the production of vinyl carbonates from cheap reagents has recently been filed. The synthesis is performed from an appropriate alcohol, carbon dioxide and acetylene in the presence of a catalyst selected from among carbonyl complexes of rhenium, manganese, tungsten, molybdenum, chromium, and iron, at a temperature under 250 1C (Scheme 1e).…”

Section: Vinyl Carbonates 21 Synthesis Of Vinyl Carbonatesmentioning

confidence: 99%

Vinyl carbonates, vinyl carbamates, and related monomers: synthesis, polymerization, and application

Husár

Liska

2012

Chem. Soc. Rev.

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Although acrylates and methacrylates are the state-of-the-art monomers for protective and decorative coatings, skin and inhalation irritancy and potential cytotoxicity of monomers present serious health hazards. Monomers like vinyl carbonates or vinyl carbamates can overcome these problems with their generally lower cytotoxicity and yet similar photoreactivity to (meth)acrylates. The reviewed classes of monomers have not attracted industry's attention until now due to expensive synthetic methods though recently developed affordable routes offer prospect for their increasing use (88 references).

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“…Other methods use enzyme‐catalyzed reactions of a different activated form, acetone O ‐(vinyloxy)carbonyl oxime in combination with the alcohol 20. The double bond can also be introduced at an activated derivative e.g., fluoro formic acid alkylether by using trimethylsilyl vinyl ether21 or acetaldehyde 13…”

Section: Resultsmentioning

confidence: 99%

“…The scientific literature is mainly concerned with monovinyl carbonates and only Olofson has prepared a divinyl carbonate based on diethylene glycol 13, 14. The use of other cross‐linking monomers is restricted to the patent literature 15.…”

Section: Introductionmentioning

confidence: 99%

Utilization and evaluation of CHO‐specific sequence databases for mass spectrometry based proteomics

Meleady

Hoffrogge

Henry

et al. 2012

Biotech & Bioengineering

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Recently released sequence information on Chinese hamster ovary (CHO) cells promises to not only facilitate our understanding of these industrially important cell factories through direct analysis of the sequence, but also to enhance existing methodologies and allow new tools to be developed. In this article we demonstrate the utilization of CHO specific sequence information to improve mass spectrometry (MS) based proteomic identification. The use of various CHO specific databases enabled the identification of 282 additional proteins, thus increasing the total number of identified proteins by 40-50%, depending on the sample source and methods used. In addition, a considerable portion of those proteins that were identified previously based on inter-species sequence homology were now identified by a larger number of peptides matched, thus increasing the confidence of identification. The new sequence information offers improved interpretation of proteomic analyses and will, in the years to come, prove vital to unraveling the CHO proteome.

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Simple one-step preparations of vinylic carbonates from aldehydes

Cited by 18 publications

References 0 publications

New catalytic alkylation of in situ generated perfluoro-alkyloxy-anions and perfluoro-carbanions

New catalytic alkylation of in situ generated perfluoro-alkyloxy-anions and perfluoro-carbanions

Vinyl carbonates, vinyl carbamates, and related monomers: synthesis, polymerization, and application

Utilization and evaluation of CHO‐specific sequence databases for mass spectrometry based proteomics

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