Heterocyclic Photochemistry in Contrast with Carbon Behavior. Regioselective Photochemical Rearrangement of an Azacyclohexadienone: Mechanistic and Exploratory Organic Photochemistry
The Type-A photochemistry of cyclohexadienones is well-studied and follows a well-established mechanistic pathway. One early example is the rearrangement of santonin to lumisantonin. Another example is the rearrangement of 4,4-diphenylcyclohexa-1,5-dienone. Remarkably, replacement of one carbon by n...
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| Veröffentlicht in: | Journal of organic chemistry 2009-08, Vol.74 (15), p.5411-5416 |
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| container_title | Journal of organic chemistry |
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| creator | Zimmerman, Howard E Shorunov, Sergey |
| description | The Type-A photochemistry of cyclohexadienones is well-studied and follows a well-established mechanistic pathway. One early example is the rearrangement of santonin to lumisantonin. Another example is the rearrangement of 4,4-diphenylcyclohexa-1,5-dienone. Remarkably, replacement of one carbon by nitrogen alters the reaction course to give a regioselective phenyl migration. |
| doi_str_mv | 10.1021/jo900901g |
| format | Article |
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Regioselective Photochemical Rearrangement of an Azacyclohexadienone: Mechanistic and Exploratory Organic Photochemistry</title><author>Zimmerman, Howard E ; Shorunov, Sergey</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-4258d167eb8eda4ce4b599e65a0f258420ded85685c7923cb18f53ce264287503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Aza Compounds - chemistry</topic><topic>Carbon - chemistry</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Kinetics and mechanisms</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Photochemistry</topic><topic>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zimmerman, Howard E</creatorcontrib><creatorcontrib>Shorunov, Sergey</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zimmerman, Howard E</au><au>Shorunov, Sergey</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Heterocyclic Photochemistry in Contrast with Carbon Behavior. Regioselective Photochemical Rearrangement of an Azacyclohexadienone: Mechanistic and Exploratory Organic Photochemistry</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-08-07</date><risdate>2009</risdate><volume>74</volume><issue>15</issue><spage>5411</spage><epage>5416</epage><pages>5411-5416</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The Type-A photochemistry of cyclohexadienones is well-studied and follows a well-established mechanistic pathway. One early example is the rearrangement of santonin to lumisantonin. Another example is the rearrangement of 4,4-diphenylcyclohexa-1,5-dienone. Remarkably, replacement of one carbon by nitrogen alters the reaction course to give a regioselective phenyl migration.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19548655</pmid><doi>10.1021/jo900901g</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2009-08, Vol.74 (15), p.5411-5416 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Aza Compounds - chemistry Carbon - chemistry Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic Compounds - chemistry Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Molecular Structure Organic chemistry Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Preparations and properties Reactivity and mechanisms Stereoisomerism |
| title | Heterocyclic Photochemistry in Contrast with Carbon Behavior. Regioselective Photochemical Rearrangement of an Azacyclohexadienone: Mechanistic and Exploratory Organic Photochemistry |
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