The direct synthesis of triorganotin compounds: Process and reaction mechanism
The reaction of tin metal with alkyl halides in the presence of a stoichiometric amount of halide ion rapidly produces very high yields of triorganotin halides. An overview of these reaction conditions and those required for the catalytic preparation of diorganotin dihalides shows that these prepara...
Gespeichert in:
| Veröffentlicht in: | Applied organometallic chemistry 1987, Vol.1 (5), p.449-458 |
|---|---|
| 1. Verfasser: | |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 458 |
|---|---|
| container_issue | 5 |
| container_start_page | 449 |
| container_title | Applied organometallic chemistry |
| container_volume | 1 |
| creator | Holland, Frank S |
| description | The reaction of tin metal with alkyl halides in the presence of a stoichiometric amount of halide ion rapidly produces very high yields of triorganotin halides. An overview of these reaction conditions and those required for the catalytic preparation of diorganotin dihalides shows that these preparations follow the normal reactivity of the alkyl halides towards nucleophiles. Both processes are satisfactorily explained by a mechanism involving tin halogenoanions as nucleophiles. A similar mechanism also explains the formation of organomagnesium and organozinc halides. |
| doi_str_mv | 10.1002/aoc.590010510 |
| format | Article |
| fullrecord | <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_aoc_590010510</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>AOC590010510</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2670-c744972446df9971141f8d825950c36443c5053ca6f64459d0edfe43547c33d23</originalsourceid><addsrcrecordid>eNp9kE1LAzEQhoMoWKtH7zl43TrZfDXeyqJVqG0PFY8hZBMb7W5KsqL99660FE-ehoHnfWd4ELomMCIA5a2JdsQVAAFO4AQNCChVgKTqFA2gFOOiFMDP0UXO7wCgBGEDNF-tHa5DcrbDedd2a5dDxtHjLoWY3kwbu9BiG5tt_GzrfIeXKVqXMzZtjZMztguxxY2za9OG3FyiM2822V0d5hC9PNyvqsditpg-VZNZYUshobCSMSVLxkTtlZKEMOLH9bjkioOlgjFqOXBqjfD9wlUNrvaOUc6kpbQu6RAV-16bYs7Jeb1NoTFppwnoXxm6l6GPMnr-Zs9vTbZm45NpbcjHUO9Ick57TO6xr7Bxu_879WRR_T1weCjkzn0fkyZ9aCGp5Pp1PtVktXx-5hXVjP4AyVp9lw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>The direct synthesis of triorganotin compounds: Process and reaction mechanism</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Holland, Frank S</creator><creatorcontrib>Holland, Frank S</creatorcontrib><description>The reaction of tin metal with alkyl halides in the presence of a stoichiometric amount of halide ion rapidly produces very high yields of triorganotin halides. An overview of these reaction conditions and those required for the catalytic preparation of diorganotin dihalides shows that these preparations follow the normal reactivity of the alkyl halides towards nucleophiles. Both processes are satisfactorily explained by a mechanism involving tin halogenoanions as nucleophiles. A similar mechanism also explains the formation of organomagnesium and organozinc halides.</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.590010510</identifier><identifier>CODEN: AOCHEX</identifier><language>eng</language><publisher>Essex: Longman Group UK Ltd</publisher><subject>Chemistry ; diorganotin dihalides ; Exact sciences and technology ; Ge, sn, pb derivatives ; Grignard ; nucleophilic ; Organic chemistry ; Organometalloidal and organometallic compounds ; organozinc ; Preparations and properties ; reaction mechanism ; synthesis ; Triorganotin halides</subject><ispartof>Applied organometallic chemistry, 1987, Vol.1 (5), p.449-458</ispartof><rights>Copyright © 1987 Longman Group UK Ltd.</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2670-c744972446df9971141f8d825950c36443c5053ca6f64459d0edfe43547c33d23</citedby><cites>FETCH-LOGICAL-c2670-c744972446df9971141f8d825950c36443c5053ca6f64459d0edfe43547c33d23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Faoc.590010510$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.590010510$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,4012,27910,27911,27912,45561,45562</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7397553$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Holland, Frank S</creatorcontrib><title>The direct synthesis of triorganotin compounds: Process and reaction mechanism</title><title>Applied organometallic chemistry</title><addtitle>Appl. Organometal. Chem</addtitle><description>The reaction of tin metal with alkyl halides in the presence of a stoichiometric amount of halide ion rapidly produces very high yields of triorganotin halides. An overview of these reaction conditions and those required for the catalytic preparation of diorganotin dihalides shows that these preparations follow the normal reactivity of the alkyl halides towards nucleophiles. Both processes are satisfactorily explained by a mechanism involving tin halogenoanions as nucleophiles. A similar mechanism also explains the formation of organomagnesium and organozinc halides.</description><subject>Chemistry</subject><subject>diorganotin dihalides</subject><subject>Exact sciences and technology</subject><subject>Ge, sn, pb derivatives</subject><subject>Grignard</subject><subject>nucleophilic</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>organozinc</subject><subject>Preparations and properties</subject><subject>reaction mechanism</subject><subject>synthesis</subject><subject>Triorganotin halides</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWKtH7zl43TrZfDXeyqJVqG0PFY8hZBMb7W5KsqL99660FE-ehoHnfWd4ELomMCIA5a2JdsQVAAFO4AQNCChVgKTqFA2gFOOiFMDP0UXO7wCgBGEDNF-tHa5DcrbDedd2a5dDxtHjLoWY3kwbu9BiG5tt_GzrfIeXKVqXMzZtjZMztguxxY2za9OG3FyiM2822V0d5hC9PNyvqsditpg-VZNZYUshobCSMSVLxkTtlZKEMOLH9bjkioOlgjFqOXBqjfD9wlUNrvaOUc6kpbQu6RAV-16bYs7Jeb1NoTFppwnoXxm6l6GPMnr-Zs9vTbZm45NpbcjHUO9Ick57TO6xr7Bxu_879WRR_T1weCjkzn0fkyZ9aCGp5Pp1PtVktXx-5hXVjP4AyVp9lw</recordid><startdate>1987</startdate><enddate>1987</enddate><creator>Holland, Frank S</creator><general>Longman Group UK Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>1987</creationdate><title>The direct synthesis of triorganotin compounds: Process and reaction mechanism</title><author>Holland, Frank S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2670-c744972446df9971141f8d825950c36443c5053ca6f64459d0edfe43547c33d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Chemistry</topic><topic>diorganotin dihalides</topic><topic>Exact sciences and technology</topic><topic>Ge, sn, pb derivatives</topic><topic>Grignard</topic><topic>nucleophilic</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>organozinc</topic><topic>Preparations and properties</topic><topic>reaction mechanism</topic><topic>synthesis</topic><topic>Triorganotin halides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Holland, Frank S</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Holland, Frank S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The direct synthesis of triorganotin compounds: Process and reaction mechanism</atitle><jtitle>Applied organometallic chemistry</jtitle><addtitle>Appl. Organometal. Chem</addtitle><date>1987</date><risdate>1987</risdate><volume>1</volume><issue>5</issue><spage>449</spage><epage>458</epage><pages>449-458</pages><issn>0268-2605</issn><eissn>1099-0739</eissn><coden>AOCHEX</coden><abstract>The reaction of tin metal with alkyl halides in the presence of a stoichiometric amount of halide ion rapidly produces very high yields of triorganotin halides. An overview of these reaction conditions and those required for the catalytic preparation of diorganotin dihalides shows that these preparations follow the normal reactivity of the alkyl halides towards nucleophiles. Both processes are satisfactorily explained by a mechanism involving tin halogenoanions as nucleophiles. A similar mechanism also explains the formation of organomagnesium and organozinc halides.</abstract><cop>Essex</cop><pub>Longman Group UK Ltd</pub><doi>10.1002/aoc.590010510</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0268-2605 |
| ispartof | Applied organometallic chemistry, 1987, Vol.1 (5), p.449-458 |
| issn | 0268-2605 1099-0739 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_aoc_590010510 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry diorganotin dihalides Exact sciences and technology Ge, sn, pb derivatives Grignard nucleophilic Organic chemistry Organometalloidal and organometallic compounds organozinc Preparations and properties reaction mechanism synthesis Triorganotin halides |
| title | The direct synthesis of triorganotin compounds: Process and reaction mechanism |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T12%3A54%3A30IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20direct%20synthesis%20of%20triorganotin%20compounds:%20Process%20and%20reaction%20mechanism&rft.jtitle=Applied%20organometallic%20chemistry&rft.au=Holland,%20Frank%20S&rft.date=1987&rft.volume=1&rft.issue=5&rft.spage=449&rft.epage=458&rft.pages=449-458&rft.issn=0268-2605&rft.eissn=1099-0739&rft.coden=AOCHEX&rft_id=info:doi/10.1002/aoc.590010510&rft_dat=%3Cwiley_cross%3EAOC590010510%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |