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This reaction is a very promising method for chemoselective deprotection of acetal type protecting groups.

Copyright © 2020 Elsevier B.V. or its licensors or contributors. Nouveaux polymères styréniques à chaînes latérales céto-énol—II. I don't know why ethylene glycol is more common, presumably it is cheaper to make. Carbonyl groups are generally protected as acetals under acidic conditions. Please reconnect. À température ambiante, c'est un liquide visqueux incolore et sans odeur, avec un goût sucré. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. https://doi.org/10.1016/j.tetlet.2004.08.035. Shahrokh Saba , James A. Ciaccio , Jennifer Espinal and Courtney E. Aman . An example of the use of this protecting group is below: The reaction works if we first protect the carbonyl. Since acetals are stable to a base (cyclic acetals moreso), the grignard reagent will only attack the Br. Find more information on the Altmetric Attention Score and how the score is calculated.

DOI: 10.1021/ed082p1057. By continuing you agree to the use of cookies. Anna C. Cunha , Leticia O. R. Pereira , Maria Cecília B. V. de Souza and Vitor F. Ferreira . You have to login with your ACS ID befor you can login with your Mendeley account. 1973, 5, 303. A  five-membered cyclic acetal is known as a dioxolane, as created in this example. Acetals are stable under reductive, basic, nucleophilic, and oxidizing (nonacidic) conditions.

L'éthylène glycol est toxique et son ingestion nécessite des soins médicaux … 2-(2-Methyl-1,3-dioxolan-2-yl)-1,1-diphenylethanol. As long as they are not treated by acids, especially aqueous acid, acetals exhibit all the lack of reactivity associated with ethers in general. Find more information about Crossref citation counts. Once we have used the Grignard reagent to attack an electrophile, we can then hydrolyse the acetal off using acid and water. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article.

Heating acetals with ethylene glycol causes the deprotection of acetal type protecting groups. Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment. Acetals as Protecting Groups. Sa formule semi-développée est HOCH2CH2OH et sa formule brute C2H6O2 (c'est le plus simple des diols). Comment on “Synthesis of 5,5-Diphenyl-4-penten-2-one: A Variation on a Classic Organic Synthesis Laboratory”. This reaction is a very promising method for chemoselective deprotection of acetal type protecting groups.

ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Once we have used the Grignard reagent to attack an electrophile, we can then hydrolyse the acetal off using acid and water. Your Mendeley pairing has expired. It is widely used as automotive antifreeze. L'éthylène glycol est fréquemment employé en tant qu'antigel, dans le liquide de refroidissement des automobiles. Notice that water needs to be distilled off for the protecting group to be fully added. When acetals such as MOM ethers, MEM ethers, and THP ethers were heated in ethylene glycol or propylene glycol, solvolysis proceeded smoothly to produce alcohols in excellent yield.

General References ・Daignault, R. A.; Eliel, E. L. Org.

6-ring diols work too. This article is cited by Since acetals are stable to a base (cyclic acetals moreso), the grignard reagent will only attack the Br. Synthèse et polymérisation de β-β-tricétones monomères. This will assume A-level knowledge of chemistry, physics and math, and aims for minimal overlap. Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment. These metrics are regularly updated to reflect usage leading up to the last few days. This forms readily even from ketones.

Copyright © 2004 Elsevier Ltd. All rights reserved.

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L'éthylène glycol ou glycol ou encore éthane-1,2-diol est le plus simple composé chimique de la famille des glycols. One of the most common acetal formation reactions you see in organic synthesis is the use of ethylene glycol. When acetals such as MOM ethers, MEM ethers, and THP ethers were heated in ethylene glycol or propylene glycol, solvolysis proceeded smoothly to produce alcohols in excellent yield.

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