Percarboxylic Acid Oxidation of α-Hydroxy-Substituted Alkoxyallenes: The Unexpected Formation of Acyloxy-Substituted 1,2-Diketones and the Synthesis of Functionalized Quinoxalines
Abstract Treatment of α-hydroxy-substituted methoxyallene derivatives with meta -chloroperbenzoic acid provided acyloxy-substituted 1,2-diketones in moderate yields. A mechanism for the formation of these unexpected products is proposed. The configuration of the enantiopure compound ( S )-1-(3-methy...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2016-05, Vol.48 (10), p.1491-1501 |
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| container_title | Synthesis (Stuttgart) |
| container_volume | 48 |
| creator | Klemme, Robby Bentz, Christoph Zukowski, Tomasz Schefzig, Luise Lentz, Dieter Reissig, Hans-Ulrich Zimmer, Reinhold |
| description | Abstract
Treatment of α-hydroxy-substituted methoxyallene derivatives with
meta
-chloroperbenzoic acid provided acyloxy-substituted 1,2-diketones in moderate yields. A mechanism for the formation of these unexpected products is proposed. The configuration of the enantiopure compound (
S
)-1-(3-methylquinoxalin-2-yl)-1-(4-nitrobenzoyloxy)propan-2-yl 3-chlorobenzoate – determined by X-ray crystal structure analysis – indicates the intermediacy of a carbenium ion during formation of the 1,2-diketones. The functionalized 1,2-diketones are valuable starting materials for a variety of products as demonstrated by the synthesis of quinoxalines, an imidazole derivative, and electron-deficient alkenes. |
| doi_str_mv | 10.1055/s-0035-1561751 |
| format | Article |
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Treatment of α-hydroxy-substituted methoxyallene derivatives with
meta
-chloroperbenzoic acid provided acyloxy-substituted 1,2-diketones in moderate yields. A mechanism for the formation of these unexpected products is proposed. The configuration of the enantiopure compound (
S
)-1-(3-methylquinoxalin-2-yl)-1-(4-nitrobenzoyloxy)propan-2-yl 3-chlorobenzoate – determined by X-ray crystal structure analysis – indicates the intermediacy of a carbenium ion during formation of the 1,2-diketones. The functionalized 1,2-diketones are valuable starting materials for a variety of products as demonstrated by the synthesis of quinoxalines, an imidazole derivative, and electron-deficient alkenes.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0035-1561751</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2016-05, Vol.48 (10), p.1491-1501</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1221-affbd57a69815e6d7b49405b13d1263b28b887c633d0f7bb36da513d2097d9fc3</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-0035-1561751.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0035-1561751$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Klemme, Robby</creatorcontrib><creatorcontrib>Bentz, Christoph</creatorcontrib><creatorcontrib>Zukowski, Tomasz</creatorcontrib><creatorcontrib>Schefzig, Luise</creatorcontrib><creatorcontrib>Lentz, Dieter</creatorcontrib><creatorcontrib>Reissig, Hans-Ulrich</creatorcontrib><creatorcontrib>Zimmer, Reinhold</creatorcontrib><title>Percarboxylic Acid Oxidation of α-Hydroxy-Substituted Alkoxyallenes: The Unexpected Formation of Acyloxy-Substituted 1,2-Diketones and the Synthesis of Functionalized Quinoxalines</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
Treatment of α-hydroxy-substituted methoxyallene derivatives with
meta
-chloroperbenzoic acid provided acyloxy-substituted 1,2-diketones in moderate yields. A mechanism for the formation of these unexpected products is proposed. The configuration of the enantiopure compound (
S
)-1-(3-methylquinoxalin-2-yl)-1-(4-nitrobenzoyloxy)propan-2-yl 3-chlorobenzoate – determined by X-ray crystal structure analysis – indicates the intermediacy of a carbenium ion during formation of the 1,2-diketones. The functionalized 1,2-diketones are valuable starting materials for a variety of products as demonstrated by the synthesis of quinoxalines, an imidazole derivative, and electron-deficient alkenes.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kMtKAzEUhoMoWKtb13kAo7k0kxl3Ra0VClXagrsht6HR6YwkM9DxnVy48QF8AJ_JDBUXgqvDOX--D_IDcErwOcGcXwSEMeOI8IQITvbAgIyYQJTgx30wiFGGRJqSQ3AUwhPGWFCWDcDHvfVaelVvu9JpONbOwPnWGdm4uoJ1Ab_e0bQzPuZo0arQuKZtrIHj8jmePt9kWdrKhku4XFu4quz2xeo-n9R-8-sY6678KyBnFF27Z9vUEYeyMrCJhkVXxRFc6LFJW-leIUv3GomH1lX1Ni4ROAYHhSyDPfmZQ7Ca3Cyvpmg2v727Gs-QJpQSJItCGS5kkqWE28QINcpGmCvCDKEJUzRVaSp0wpjBhVCKJUbyGFKcCZMVmg3B-c6rfR2Ct0X-4t1G-i4nOO9bz0Pet57_tB4BtAOatbMbmz_VrY8fCP-9_wZ1YIlY</recordid><startdate>20160518</startdate><enddate>20160518</enddate><creator>Klemme, Robby</creator><creator>Bentz, Christoph</creator><creator>Zukowski, Tomasz</creator><creator>Schefzig, Luise</creator><creator>Lentz, Dieter</creator><creator>Reissig, Hans-Ulrich</creator><creator>Zimmer, Reinhold</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20160518</creationdate><title>Percarboxylic Acid Oxidation of α-Hydroxy-Substituted Alkoxyallenes: The Unexpected Formation of Acyloxy-Substituted 1,2-Diketones and the Synthesis of Functionalized Quinoxalines</title><author>Klemme, Robby ; Bentz, Christoph ; Zukowski, Tomasz ; Schefzig, Luise ; Lentz, Dieter ; Reissig, Hans-Ulrich ; Zimmer, Reinhold</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1221-affbd57a69815e6d7b49405b13d1263b28b887c633d0f7bb36da513d2097d9fc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Klemme, Robby</creatorcontrib><creatorcontrib>Bentz, Christoph</creatorcontrib><creatorcontrib>Zukowski, Tomasz</creatorcontrib><creatorcontrib>Schefzig, Luise</creatorcontrib><creatorcontrib>Lentz, Dieter</creatorcontrib><creatorcontrib>Reissig, Hans-Ulrich</creatorcontrib><creatorcontrib>Zimmer, Reinhold</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Klemme, Robby</au><au>Bentz, Christoph</au><au>Zukowski, Tomasz</au><au>Schefzig, Luise</au><au>Lentz, Dieter</au><au>Reissig, Hans-Ulrich</au><au>Zimmer, Reinhold</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Percarboxylic Acid Oxidation of α-Hydroxy-Substituted Alkoxyallenes: The Unexpected Formation of Acyloxy-Substituted 1,2-Diketones and the Synthesis of Functionalized Quinoxalines</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2016-05-18</date><risdate>2016</risdate><volume>48</volume><issue>10</issue><spage>1491</spage><epage>1501</epage><pages>1491-1501</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
Treatment of α-hydroxy-substituted methoxyallene derivatives with
meta
-chloroperbenzoic acid provided acyloxy-substituted 1,2-diketones in moderate yields. A mechanism for the formation of these unexpected products is proposed. The configuration of the enantiopure compound (
S
)-1-(3-methylquinoxalin-2-yl)-1-(4-nitrobenzoyloxy)propan-2-yl 3-chlorobenzoate – determined by X-ray crystal structure analysis – indicates the intermediacy of a carbenium ion during formation of the 1,2-diketones. The functionalized 1,2-diketones are valuable starting materials for a variety of products as demonstrated by the synthesis of quinoxalines, an imidazole derivative, and electron-deficient alkenes.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0035-1561751</doi><tpages>11</tpages></addata></record> |
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| source | Thieme Connect Journals |
| title | Percarboxylic Acid Oxidation of α-Hydroxy-Substituted Alkoxyallenes: The Unexpected Formation of Acyloxy-Substituted 1,2-Diketones and the Synthesis of Functionalized Quinoxalines |
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