Nucleophilicity Parameters for Alkyl and Aryl Isocyanides
How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2007-05, Vol.46 (19), p.3563-3566 |
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| container_issue | 19 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Tumanov, Vasily V. Tishkov, Alexander A. Mayr, Herbert |
| description | How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers (see the diagram for a comparison of the nucleophilicity N of various isocyanides; Ts=toluene‐4‐sulfonyl). |
| doi_str_mv | 10.1002/anie.200605205 |
| format | Article |
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The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers (see the diagram for a comparison of the nucleophilicity N of various isocyanides; Ts=toluene‐4‐sulfonyl).</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200605205</identifier><identifier>PMID: 17394269</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>carbocations ; isocyanides ; kinetics ; nitrilium ions ; reactivity</subject><ispartof>Angewandte Chemie International Edition, 2007-05, Vol.46 (19), p.3563-3566</ispartof><rights>Copyright © 2007 WILEY‐VCH Verlag GmbH & Co. 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The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers (see the diagram for a comparison of the nucleophilicity N of various isocyanides; Ts=toluene‐4‐sulfonyl).</description><subject>carbocations</subject><subject>isocyanides</subject><subject>kinetics</subject><subject>nitrilium ions</subject><subject>reactivity</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAQxS0EoqWwMqJMbCn-iON4LKWESlXpAFRisRz3LELTptitIP89rlIBG9OddL_37ukhdElwn2BMb_S6hD7FOMWcYn6EuoRTEjMh2HHYE8ZikXHSQWfevwc-y3B6ijpEMJnQVHaRnO5MBfXmraxKU26baKadXsEWnI9s7aJBtWyqSK8X0cCFZexr04SfC_Dn6MTqysPFYfbQ8_3oafgQTx7z8XAwiQ2VKY8tcGoTJnFmJIOCEk4KG05ZZrHUeFEwLiwOd8Ot1FRowNhAKnjIbovCsB66bn03rv7Ygd-qVekNVJVeQ73zSuBEUpaKAPZb0LjaewdWbVy50q5RBKt9WWpflvopKwiuDs67YgWLX_zQTgBkC3yWFTT_2KnBdDz6ax632tJv4etHq91ShayCq_k0V6_53ct8lifqln0DShWE7w</recordid><startdate>20070504</startdate><enddate>20070504</enddate><creator>Tumanov, Vasily V.</creator><creator>Tishkov, Alexander A.</creator><creator>Mayr, Herbert</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070504</creationdate><title>Nucleophilicity Parameters for Alkyl and Aryl Isocyanides</title><author>Tumanov, Vasily V. ; Tishkov, Alexander A. ; Mayr, Herbert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2965-fe52f43908c93eb2151bfc2988f09a0db357f0390c5f9a27ae00ce675433fbbc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>carbocations</topic><topic>isocyanides</topic><topic>kinetics</topic><topic>nitrilium ions</topic><topic>reactivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tumanov, Vasily V.</creatorcontrib><creatorcontrib>Tishkov, Alexander A.</creatorcontrib><creatorcontrib>Mayr, Herbert</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tumanov, Vasily V.</au><au>Tishkov, Alexander A.</au><au>Mayr, Herbert</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nucleophilicity Parameters for Alkyl and Aryl Isocyanides</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angewandte Chemie International Edition</addtitle><date>2007-05-04</date><risdate>2007</risdate><volume>46</volume><issue>19</issue><spage>3563</spage><epage>3566</epage><pages>3563-3566</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers (see the diagram for a comparison of the nucleophilicity N of various isocyanides; Ts=toluene‐4‐sulfonyl).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>17394269</pmid><doi>10.1002/anie.200605205</doi><tpages>4</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | carbocations isocyanides kinetics nitrilium ions reactivity |
| title | Nucleophilicity Parameters for Alkyl and Aryl Isocyanides |
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