Polymer-supported Azide Research Articles

Polymer-Supported Azide and Copper(I): Green Reusable Reagent and Catalyst for Click Cyclization

In this work, polymer-supported copper(I) iodide catalyst and macroporous polymer-supported azide reagent were used to simplify the synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from α-bromo ketones/amides/esters following green chemistry principles. This new one-pot protocol facilitates the workup of the reaction and provides the products in short times and excellent yields. Heterogeneous catalyst and reagent can be reused at least for five runs without significant yield decreases.

Rapid and facile synthesis of acyl azides from acyl halides using a polymer-supported azide ion under heterogeneous conditions

In this article a rapid and facile method for synthesis of acyl azide is described. The cross-linked poly(N-methyl-4-vinylpyridinium) azide ion, [P4-VP]N3 is prepared and used as an efficient polymeric reagent for synthesis of acyl azides from acyl halides at room temperature under heterogeneous conditions. Various benzoyl halides, with electron-withdrawing groups as well as electron-donating groups, were transformed into the corresponding benzoyl azides in high to excellent yields in short reaction times. The acyl azide products were characterized by FT-IR, and some of them were also characterized by 1H-and/or 13C-NMR spectroscopy, and physical properties were compared to literature values of known compounds. The spent polymeric reagents can be regenerated and reused for several times without losing their activity. Relative to the reported methods, the present method has the advantages of operational simplicity, mild reaction conditions, fast reaction rates, simple reaction work-up and lower hazardous and potentially explosive nature. Also the present method is the first procedure for the synthesis of acyl azides from acyl halides by using a polymer-supported azide ion under heterogeneous conditions.

Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β- l-4-aminopent-2-eno glyceropyranosides

Starting from alkyl α- d-4- O-methanesulphonylpent-2-eno glyceropyranosides 13a– c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a– c and 15a– c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl α- d-hex-2-eno erythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl β- d-4- O-methanesulphonylpent-2-eno glyceropyranosides 21a– c, azides 22a– c were exclusively obtained, and subsequently converted into the corresponding amino derivatives 23a– c. The behaviour of β-anomers 21a– c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations.

Regioselective ring opening of polycyclic aromatic hydrocarbon epoxides by polymer-supported azide anion

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRegioselective ring opening of polycyclic aromatic hydrocarbon epoxides by polymer-supported azide anionMaheshkumar Lakshman, Durgesh V. Nadkarni, and Roland E. LehrCite this: J. Org. Chem. 1990, 55, 16, 4892–4897Publication Date (Print):August 1, 1990Publication History Published online1 May 2002Published inissue 1 August 1990https://doi.org/10.1021/jo00303a025RIGHTS & PERMISSIONSArticle Views438Altmetric-Citations30LEARN 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 InReddit PDF (871 KB) Get e-Alerts Get e-Alerts