Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups
David A. BabbRichard A. BartschJames J. CollierDhimant DesaiSadik ElshaniaMi‐Ja GooJohnny L. HallmanGwi Suk HeoXiaowu HuangVincent J. HuberHong‐Sik HwangRussell J. JohnsonYung LiuMichael J. PugiaQiang Zhao
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Abstract Structurally related dibenzo‐16‐crown‐5 lariat ethers with pendant ester and ether groups are prepared. Structural variations within the series of alkyl lariat ether esters include changes in the O‐alkyl group, attachment site and nature of the lipophilic group, and length of the spacer, which connects the ester group to the polyether framework. Also synthesized are bis(crown ether) diesters with two dibenzo‐16‐crown‐5 or two dicyclohexano‐16‐crown‐5 units and two ester groups connected to each other by a linker of varying length. Synthetic strategies for the preparation of these lariat ethers with pendant ester‐ and ether‐containing side arms are described.Keywords:
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Williamson ether synthesis
Abstract The crystal structure of the KSCN complex of 1,5‐bis(N‐monoaza‐15‐crown‐5)‐3‐oxapentane (BOA15C5) is investigated and discussed in detail.
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Abstract The article contains sections titled: 1. Introduction 2. Properties 2.1. Physical Properties 2.2. Chemical Properties 2.2.1 General Aspects 2.2.2 Peroxide Formation Tendency of Ethers 3. Synthesis 4. Individual Aliphatic Ethers 4.1. Diethyl Ether 4.2. Diisopropyl Ether 4.3. Other Aliphatic Ethers 4.3.1. Di‐ n ‐propyl Ether 4.3.2. Di‐ n ‐butyl Ether 4.3.3. Diamyl Ether 4.4. Chloroalkyl Ethers 4.4.1. Bis(chloromethyl) Ether 4.4.2. Bis(2‐chloroethyl) Ether 4.4.3. Bis(2‐chloroisopropyl) Ether 5. Toxicology
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Abstract Three types of bis(crown ether) dyes bearing one or two azophenol units were synthesized, which may be expected to show different cation-complexing properties from the corresponding monocyclic crown ether dyes. The extraction of alkali and alkaline-earth metal salts with the crown ether dyes suggested that some cooperative action of the two adjacent crown ether moieties of the bis(crown ether)s occurs on complexing metal cations, although the bis(crown ether) effect is not very remarkable.
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Abstract Structurally related dibenzo‐16‐crown‐5 lariat ethers with pendant ester and ether groups are prepared. Structural variations within the series of alkyl lariat ether esters include changes in the O‐alkyl group, attachment site and nature of the lipophilic group, and length of the spacer, which connects the ester group to the polyether framework. Also synthesized are bis(crown ether) diesters with two dibenzo‐16‐crown‐5 or two dicyclohexano‐16‐crown‐5 units and two ester groups connected to each other by a linker of varying length. Synthetic strategies for the preparation of these lariat ethers with pendant ester‐ and ether‐containing side arms are described.
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Williamson ether synthesis
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New blood for crown ether chemistry! Beside the well-known organocrown ether sandwich complexes 1 there now exist topologically equivalent metallacrown ether complexes 2. These metallasandwich complexes are generated in a one-pot reaction by spontanous self-assembly and in one case have been unambiguously characterized by a crystallographic structure analysis.
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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Preparation of Allyl Phenyl Ether and 2-Allylphenol Using the Williamson Ether Synthesis and Claisen RearrangementElizabeth M. Sanford , Christina C. Lis , and Nikolas R. McPherson View Author Information Department of Chemistry, Hope College, Holland, MI 49422-9000Cite this: J. Chem. Educ. 2009, 86, 12, 1422Publication Date (Web):December 1, 2009Publication History Received3 August 2009Published online1 December 2009Published inissue 1 December 2009https://pubs.acs.org/doi/10.1021/ed086p1422https://doi.org/10.1021/ed086p1422research-articleACS PublicationsRequest reuse permissionsArticle Views5148Altmetric-Citations17LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. 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. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Allyl group,Claisen rearrangement,Ethers,Organic synthesis,Phenyls Get e-Alerts
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Abstract Based on considerations of membrane activity, a DDT analogue containing crown ether moieties has been conceived and prepared. The preparation of the compound represents a novel route for obtaining crown ether derivatives.
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