Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)

Abstract The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroa...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Synthesis (Stuttgart) 2006-10, Vol.2006 (19), p.3305-3308
Hauptverfasser:	Hwu, Jih Ru, Josephrajan, Thainashmuthu, Tsay, Shwu-Chen
Format:	Artikel
Sprache:	eng
Schlagworte:	special topic
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	3308
container_issue	19
container_start_page	3305
container_title	Synthesis (Stuttgart)
container_volume	2006
creator	Hwu, Jih Ru Josephrajan, Thainashmuthu Tsay, Shwu-Chen
description	Abstract The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions.
doi_str_mv	10.1055/s-2006-950225
format	Article
fullrecord	<record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_2006_950225</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_2006_950225</sourcerecordid><originalsourceid>FETCH-LOGICAL-c274t-b706cb065378cbfc208cd3fcb8dffd6896ae82d54155a71e6b203f43ffaf83ce3</originalsourceid><addsrcrecordid>eNp1kEtLAzEYRYMoWKtL91kqNPolmUwySxl8YVHBCu6GTB6YOk3KZCrUX2_LuHV14XK4XA5C5xSuKAhxnQkDKEklgDFxgCa04JIwCh-HaALAKyKVosfoJOclAEjGqwlavIUumBRJrQfdbX-cxXWK367PIUWcPH4OQ5923WqdNtFmHOKQ8JMbUnQZ62jxa-q2F3TGiQ1fY315io687rI7-8sper-7XdQPZP5y_1jfzIlhshhIK6E0LZSCS2VabxgoY7k3rbLe21JVpXaKWVFQIbSkrmwZcF9w77VX3Dg-RWTcNX3KuXe-WfdhpfttQ6HZK2lys1fSjEp2_Gzkh8_gVq5Zpk0fdwf_wX8BqH5irA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)</title><source>Thieme Connect Journals</source><creator>Hwu, Jih Ru ; Josephrajan, Thainashmuthu ; Tsay, Shwu-Chen</creator><creatorcontrib>Hwu, Jih Ru ; Josephrajan, Thainashmuthu ; Tsay, Shwu-Chen</creatorcontrib><description>Abstract The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-2006-950225</identifier><language>eng</language><subject>special topic</subject><ispartof>Synthesis (Stuttgart), 2006-10, Vol.2006 (19), p.3305-3308</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c274t-b706cb065378cbfc208cd3fcb8dffd6896ae82d54155a71e6b203f43ffaf83ce3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-950225.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2006-950225$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3004,3005,27901,27902,54534,54535</link.rule.ids></links><search><creatorcontrib>Hwu, Jih Ru</creatorcontrib><creatorcontrib>Josephrajan, Thainashmuthu</creatorcontrib><creatorcontrib>Tsay, Shwu-Chen</creatorcontrib><title>Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions.</description><subject>special topic</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp1kEtLAzEYRYMoWKtL91kqNPolmUwySxl8YVHBCu6GTB6YOk3KZCrUX2_LuHV14XK4XA5C5xSuKAhxnQkDKEklgDFxgCa04JIwCh-HaALAKyKVosfoJOclAEjGqwlavIUumBRJrQfdbX-cxXWK367PIUWcPH4OQ5923WqdNtFmHOKQ8JMbUnQZ62jxa-q2F3TGiQ1fY315io687rI7-8sper-7XdQPZP5y_1jfzIlhshhIK6E0LZSCS2VabxgoY7k3rbLe21JVpXaKWVFQIbSkrmwZcF9w77VX3Dg-RWTcNX3KuXe-WfdhpfttQ6HZK2lys1fSjEp2_Gzkh8_gVq5Zpk0fdwf_wX8BqH5irA</recordid><startdate>20061004</startdate><enddate>20061004</enddate><creator>Hwu, Jih Ru</creator><creator>Josephrajan, Thainashmuthu</creator><creator>Tsay, Shwu-Chen</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20061004</creationdate><title>Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)</title><author>Hwu, Jih Ru ; Josephrajan, Thainashmuthu ; Tsay, Shwu-Chen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-b706cb065378cbfc208cd3fcb8dffd6896ae82d54155a71e6b203f43ffaf83ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>special topic</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hwu, Jih Ru</creatorcontrib><creatorcontrib>Josephrajan, Thainashmuthu</creatorcontrib><creatorcontrib>Tsay, Shwu-Chen</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hwu, Jih Ru</au><au>Josephrajan, Thainashmuthu</au><au>Tsay, Shwu-Chen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2006-10-04</date><risdate>2006</risdate><volume>2006</volume><issue>19</issue><spage>3305</spage><epage>3308</epage><pages>3305-3308</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions.</abstract><doi>10.1055/s-2006-950225</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0039-7881
ispartof	Synthesis (Stuttgart), 2006-10, Vol.2006 (19), p.3305-3308
issn	0039-7881 1437-210X
language	eng
recordid	cdi_crossref_primary_10_1055_s_2006_950225
source	Thieme Connect Journals
subjects	special topic
title	Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T14%3A43%3A11IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Silicon-Catalyzed%20Conversion%20of%20Nitro%20Compounds%20into%20Ketones%20and%20Poly(1,3-diketones)&rft.jtitle=Synthesis%20(Stuttgart)&rft.au=Hwu,%20Jih%20Ru&rft.date=2006-10-04&rft.volume=2006&rft.issue=19&rft.spage=3305&rft.epage=3308&rft.pages=3305-3308&rft.issn=0039-7881&rft.eissn=1437-210X&rft_id=info:doi/10.1055/s-2006-950225&rft_dat=%3Cthieme_cross%3E10_1055_s_2006_950225%3C/thieme_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