Carbon–carbon double bond isomerization in heterocyclic hydrazine derivatives
Double bond isomerization by in situ generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N–N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generall...
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Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-05, Vol.54 (5), p.572-575 |
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container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
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creator | Ilisson, Mihkel Tomson, Kristjan Tamm, Tarmo Mäeorg, Uno |
description | Double bond isomerization by
in situ
generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N–N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generally favored, but in some cases, the reaction pathway is presumably also highly dependent of steric interactions. With the current method, two novel enehydrazide heterocycles and one enehydrazine heterocycle were produced and characterized. |
doi_str_mv | 10.1007/s10593-018-2308-9 |
format | Article |
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in situ
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in situ
generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N–N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generally favored, but in some cases, the reaction pathway is presumably also highly dependent of steric interactions. With the current method, two novel enehydrazide heterocycles and one enehydrazine heterocycle were produced and characterized.</description><subject>Carbon</subject><subject>Chemical properties</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Heterocyclic compounds</subject><subject>Hydrazines</subject><subject>Isomerization</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Platinum group compounds</subject><subject>Ruthenium</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kEtKBDEQhoMoOD4O4K7BdWvlnV7K4AsEN7oO3Un1TGSmo0mPMK68gzf0JEZbcCVZVCX5vqT4CTmhcEYB9HmmIBteAzU142DqZofMqNS8NlzyXTIDgKbmlLF9cpDzU9lqasSM3M_b1MXh8_3D_TSVj5tuhVVpfRVyXGMKb-0Yyk0YqiWOmKLbulVw1XLrU_sWBqx8gV4L9Ir5iOz17Srj8W89JI9Xlw_zm_ru_vp2fnFXOy7lWBuJ3msteC-dAATPjSrj-k44L7AD03TYNFyhEK1qfC80lMJ6rQ2lVEl-SE6nd59TfNlgHu1T3KShfGkZKM2AKsYKdTZRi3aFNgx9HFPryvK4Di4O2IdyfiGFAqWMNkWgk-BSzDlhb59TWLdpaynY76DtFLQtQdvvoG1THDY5ubDDAtPfKP9LXzPZgVE</recordid><startdate>20180501</startdate><enddate>20180501</enddate><creator>Ilisson, Mihkel</creator><creator>Tomson, Kristjan</creator><creator>Tamm, Tarmo</creator><creator>Mäeorg, Uno</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20180501</creationdate><title>Carbon–carbon double bond isomerization in heterocyclic hydrazine derivatives</title><author>Ilisson, Mihkel ; Tomson, Kristjan ; Tamm, Tarmo ; Mäeorg, Uno</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-85edd7743f5c40e0d386157db4cd4eb089be9936e44a69df47069d2f778111653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Carbon</topic><topic>Chemical properties</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Heterocyclic compounds</topic><topic>Hydrazines</topic><topic>Isomerization</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Platinum group compounds</topic><topic>Ruthenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ilisson, Mihkel</creatorcontrib><creatorcontrib>Tomson, Kristjan</creatorcontrib><creatorcontrib>Tamm, Tarmo</creatorcontrib><creatorcontrib>Mäeorg, Uno</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ilisson, Mihkel</au><au>Tomson, Kristjan</au><au>Tamm, Tarmo</au><au>Mäeorg, Uno</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbon–carbon double bond isomerization in heterocyclic hydrazine derivatives</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2018-05-01</date><risdate>2018</risdate><volume>54</volume><issue>5</issue><spage>572</spage><epage>575</epage><pages>572-575</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>Double bond isomerization by
in situ
generated ruthenium hydride catalyst in 6- to 9-membered hydrazine heterocycles including an endocyclic N–N bond was investigated. Based on the results of the experiments, a conclusion was made that the generation of resonance-stabilized enehydrazides is generally favored, but in some cases, the reaction pathway is presumably also highly dependent of steric interactions. With the current method, two novel enehydrazide heterocycles and one enehydrazine heterocycle were produced and characterized.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-018-2308-9</doi><tpages>4</tpages></addata></record> |
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subjects | Carbon Chemical properties Chemistry Chemistry and Materials Science Heterocyclic compounds Hydrazines Isomerization Organic Chemistry Pharmacy Platinum group compounds Ruthenium |
title | Carbon–carbon double bond isomerization in heterocyclic hydrazine derivatives |
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