Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents
The report briefly reviews results and publications from a research study on anion attack on conjugated systems. In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition...
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description | The report briefly reviews results and publications from a research study on anion attack on conjugated systems. In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition of cyanide ion to give carbanions which can be transformed into other substances, including the products of cyanation and hydrocyanation of the original hydrocarbons. Aromatic nitriles, particularly those containing polynuclear aromatic systems, also undergo addition of cyanide ion in a process which is useful in synthesis, including the synthesis of C-14 labelled nitriles. Aromatic ketones react with cyanide ion similarly but less readily, and aromatic nitro compounds are more reactive than nitriles and can be converted to a number of further transformation products. (Modified author abstract) |
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In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition of cyanide ion to give carbanions which can be transformed into other substances, including the products of cyanation and hydrocyanation of the original hydrocarbons. Aromatic nitriles, particularly those containing polynuclear aromatic systems, also undergo addition of cyanide ion in a process which is useful in synthesis, including the synthesis of C-14 labelled nitriles. Aromatic ketones react with cyanide ion similarly but less readily, and aromatic nitro compounds are more reactive than nitriles and can be converted to a number of further transformation products. (Modified author abstract)</description><language>eng</language><subject>ADDITION REACTIONS ; ALKENES ; ANTHRACENES ; AROMATIC COMPOUNDS ; CARBANIONS ; CHEMICAL REACTIONS ; CYANIDES ; IONS ; KETONES ; NITRILES ; NITRO COMPOUNDS ; Organic Chemistry ; SYNTHESIS(CHEMISTRY)</subject><creationdate>1973</creationdate><rights>APPROVED FOR PUBLIC RELEASE</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,780,885,27567,27568</link.rule.ids><linktorsrc>$$Uhttps://apps.dtic.mil/sti/citations/AD0768799$$EView_record_in_DTIC$$FView_record_in_$$GDTIC$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Snyder,Harold R</creatorcontrib><creatorcontrib>ILLINOIS UNIV URBANA</creatorcontrib><title>Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents</title><description>The report briefly reviews results and publications from a research study on anion attack on conjugated systems. In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition of cyanide ion to give carbanions which can be transformed into other substances, including the products of cyanation and hydrocyanation of the original hydrocarbons. Aromatic nitriles, particularly those containing polynuclear aromatic systems, also undergo addition of cyanide ion in a process which is useful in synthesis, including the synthesis of C-14 labelled nitriles. Aromatic ketones react with cyanide ion similarly but less readily, and aromatic nitro compounds are more reactive than nitriles and can be converted to a number of further transformation products. (Modified author abstract)</description><subject>ADDITION REACTIONS</subject><subject>ALKENES</subject><subject>ANTHRACENES</subject><subject>AROMATIC COMPOUNDS</subject><subject>CARBANIONS</subject><subject>CHEMICAL REACTIONS</subject><subject>CYANIDES</subject><subject>IONS</subject><subject>KETONES</subject><subject>NITRILES</subject><subject>NITRO COMPOUNDS</subject><subject>Organic Chemistry</subject><subject>SYNTHESIS(CHEMISTRY)</subject><fulltext>true</fulltext><rsrctype>report</rsrctype><creationdate>1973</creationdate><recordtype>report</recordtype><sourceid>1RU</sourceid><recordid>eNqFTL0KwjAQ7uIg6hs43AsIgmDtGKqik6Du5WwueNBeJDkrfXtjdXf6_r9x9jwT1speIngHJtEOlSycGnIsXAOKBRN8i5rEpY9KbYQX6x3KHoUtwdHL0PqaFBRZoMRwS_HnNynzCH7Y-6Yj0TjNRg6bSLMfTrL5fnctDwubWlVUFtLKbJf5epMXxepP_AajoUGD</recordid><startdate>19730926</startdate><enddate>19730926</enddate><creator>Snyder,Harold R</creator><scope>1RU</scope><scope>BHM</scope></search><sort><creationdate>19730926</creationdate><title>Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents</title><author>Snyder,Harold R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-dtic_stinet_AD07687993</frbrgroupid><rsrctype>reports</rsrctype><prefilter>reports</prefilter><language>eng</language><creationdate>1973</creationdate><topic>ADDITION REACTIONS</topic><topic>ALKENES</topic><topic>ANTHRACENES</topic><topic>AROMATIC COMPOUNDS</topic><topic>CARBANIONS</topic><topic>CHEMICAL REACTIONS</topic><topic>CYANIDES</topic><topic>IONS</topic><topic>KETONES</topic><topic>NITRILES</topic><topic>NITRO COMPOUNDS</topic><topic>Organic Chemistry</topic><topic>SYNTHESIS(CHEMISTRY)</topic><toplevel>online_resources</toplevel><creatorcontrib>Snyder,Harold R</creatorcontrib><creatorcontrib>ILLINOIS UNIV URBANA</creatorcontrib><collection>DTIC Technical Reports</collection><collection>DTIC STINET</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Snyder,Harold R</au><aucorp>ILLINOIS UNIV URBANA</aucorp><format>book</format><genre>unknown</genre><ristype>RPRT</ristype><btitle>Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents</btitle><date>1973-09-26</date><risdate>1973</risdate><abstract>The report briefly reviews results and publications from a research study on anion attack on conjugated systems. In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition of cyanide ion to give carbanions which can be transformed into other substances, including the products of cyanation and hydrocyanation of the original hydrocarbons. Aromatic nitriles, particularly those containing polynuclear aromatic systems, also undergo addition of cyanide ion in a process which is useful in synthesis, including the synthesis of C-14 labelled nitriles. Aromatic ketones react with cyanide ion similarly but less readily, and aromatic nitro compounds are more reactive than nitriles and can be converted to a number of further transformation products. (Modified author abstract)</abstract><oa>free_for_read</oa></addata></record> |
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subjects | ADDITION REACTIONS ALKENES ANTHRACENES AROMATIC COMPOUNDS CARBANIONS CHEMICAL REACTIONS CYANIDES IONS KETONES NITRILES NITRO COMPOUNDS Organic Chemistry SYNTHESIS(CHEMISTRY) |
title | Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents |
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