Novel Fragmentation Reaction of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones
2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo lithium hydroxide- and lithium alkoxide-induced fragmentation reactions to provide butenolides, γ-hydroxycyclohexenones, and/or γ-butyrolactones. In general, product distribution is governed by two factors: (1) the nature of...
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| Veröffentlicht in: | Journal of organic chemistry 2004-10, Vol.69 (22), p.7728-7733 |
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| container_issue | 22 |
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| container_title | Journal of organic chemistry |
| container_volume | 69 |
| creator | Khim, Seock-Kyu Dai, Mingshi Zhang, Xuqing Chen, Lei Pettus, Liping Thakkar, Kshitij Schultz, Arthur G |
| description | 2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo lithium hydroxide- and lithium alkoxide-induced fragmentation reactions to provide butenolides, γ-hydroxycyclohexenones, and/or γ-butyrolactones. In general, product distribution is governed by two factors: (1) the nature of nucleophiles and (2) the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanones. Lithium hydroxide-induced fragmentation provides butenolides and γ-hydroxycyclohexenones. In contrast, lithium alkoxide-promoted fragmentation results in predominantly 5-substituted γ-butyrolactones along with a small amount of butenolides in limited cases. Fragmentation products induced by lithium hydroxide are largely influenced by the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanone ring. The bulky substituents render the exclusive formation of butenolides. |
| doi_str_mv | 10.1021/jo0490853 |
| format | Article |
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In general, product distribution is governed by two factors: (1) the nature of nucleophiles and (2) the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanones. Lithium hydroxide-induced fragmentation provides butenolides and γ-hydroxycyclohexenones. In contrast, lithium alkoxide-promoted fragmentation results in predominantly 5-substituted γ-butyrolactones along with a small amount of butenolides in limited cases. Fragmentation products induced by lithium hydroxide are largely influenced by the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanone ring. The bulky substituents render the exclusive formation of butenolides.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0490853</identifier><identifier>PMID: 15498003</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Catalysis ; Chemistry ; Cyclization ; Cyclohexanones - chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Lactones - chemistry ; Lithium - chemistry ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2004-10, Vol.69 (22), p.7728-7733</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-56f88123a4f0b8a11ea082b83842076ddeac91ea426e83f1ab9c22896e32e9a13</citedby><cites>FETCH-LOGICAL-a379t-56f88123a4f0b8a11ea082b83842076ddeac91ea426e83f1ab9c22896e32e9a13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0490853$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0490853$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16219232$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15498003$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Khim, Seock-Kyu</creatorcontrib><creatorcontrib>Dai, Mingshi</creatorcontrib><creatorcontrib>Zhang, Xuqing</creatorcontrib><creatorcontrib>Chen, Lei</creatorcontrib><creatorcontrib>Pettus, Liping</creatorcontrib><creatorcontrib>Thakkar, Kshitij</creatorcontrib><creatorcontrib>Schultz, Arthur G</creatorcontrib><title>Novel Fragmentation Reaction of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo lithium hydroxide- and lithium alkoxide-induced fragmentation reactions to provide butenolides, γ-hydroxycyclohexenones, and/or γ-butyrolactones. In general, product distribution is governed by two factors: (1) the nature of nucleophiles and (2) the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanones. Lithium hydroxide-induced fragmentation provides butenolides and γ-hydroxycyclohexenones. In contrast, lithium alkoxide-promoted fragmentation results in predominantly 5-substituted γ-butyrolactones along with a small amount of butenolides in limited cases. Fragmentation products induced by lithium hydroxide are largely influenced by the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanone ring. The bulky substituents render the exclusive formation of butenolides.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Cyclohexanones - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Lactones - chemistry</subject><subject>Lithium - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtuGyEUBmBUNWqcy6IvUM2mlSKVBA4zGJZRbm1k5V6pO3SGYdpJ8JDCOLLfvsS24k3YgA6ffh39hHzm7JAz4EePgZWaqUp8ICNeAaNSs_IjGTEGQAVIsU12Unpk-VRV9Yls86rUijExIngVXpwvziP-mbp-wKELfXHn0C4foS2AHvunhacF9k0B30t62uFyIGgXmkA5DfNgF9aHv26OPX0lFmMdfM4IvUt7ZKtFn9z--t4lv87PHk5-0Mn1xc-T4wlFMdYDrWSrFAeBZctqhZw7ZApqJVQJbCybJu-k87AE6ZRoOdbaAigtnQCnkYtd8m2V-xzDv5lLg5l2yTrvsXdhloyUWnOQOsODFbQxpBRda55jN8W4MJyZ1z7NW5_ZflmHzuqpazZyXWAGX9cAk0XfRuxtlzZOAtcgIDu6cl0a3PztH-OTkWMxrszDzb25vBe_b2_klSk3uWhT3mcW-9zdOwv-ByXNlao</recordid><startdate>20041029</startdate><enddate>20041029</enddate><creator>Khim, Seock-Kyu</creator><creator>Dai, Mingshi</creator><creator>Zhang, Xuqing</creator><creator>Chen, Lei</creator><creator>Pettus, Liping</creator><creator>Thakkar, Kshitij</creator><creator>Schultz, Arthur G</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20041029</creationdate><title>Novel Fragmentation Reaction of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones</title><author>Khim, Seock-Kyu ; Dai, Mingshi ; Zhang, Xuqing ; Chen, Lei ; Pettus, Liping ; Thakkar, Kshitij ; Schultz, Arthur G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-56f88123a4f0b8a11ea082b83842076ddeac91ea426e83f1ab9c22896e32e9a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Cyclohexanones - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Lactones - chemistry</topic><topic>Lithium - chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khim, Seock-Kyu</creatorcontrib><creatorcontrib>Dai, Mingshi</creatorcontrib><creatorcontrib>Zhang, Xuqing</creatorcontrib><creatorcontrib>Chen, Lei</creatorcontrib><creatorcontrib>Pettus, Liping</creatorcontrib><creatorcontrib>Thakkar, Kshitij</creatorcontrib><creatorcontrib>Schultz, Arthur G</creatorcontrib><collection>Istex</collection><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>Khim, Seock-Kyu</au><au>Dai, Mingshi</au><au>Zhang, Xuqing</au><au>Chen, Lei</au><au>Pettus, Liping</au><au>Thakkar, Kshitij</au><au>Schultz, Arthur G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Fragmentation Reaction of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-10-29</date><risdate>2004</risdate><volume>69</volume><issue>22</issue><spage>7728</spage><epage>7733</epage><pages>7728-7733</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo lithium hydroxide- and lithium alkoxide-induced fragmentation reactions to provide butenolides, γ-hydroxycyclohexenones, and/or γ-butyrolactones. In general, product distribution is governed by two factors: (1) the nature of nucleophiles and (2) the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanones. Lithium hydroxide-induced fragmentation provides butenolides and γ-hydroxycyclohexenones. In contrast, lithium alkoxide-promoted fragmentation results in predominantly 5-substituted γ-butyrolactones along with a small amount of butenolides in limited cases. Fragmentation products induced by lithium hydroxide are largely influenced by the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanone ring. The bulky substituents render the exclusive formation of butenolides.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15498003</pmid><doi>10.1021/jo0490853</doi><tpages>6</tpages></addata></record> |
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| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Catalysis Chemistry Cyclization Cyclohexanones - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones - chemistry Lithium - chemistry Molecular Structure Organic chemistry Preparations and properties Stereoisomerism |
| title | Novel Fragmentation Reaction of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones |
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