Preparation of donor-acceptor-substituted vinylcyclobutanes
2‐Methylen‐1,3‐dioxolane (1) and the methyl acrylates or crotonates 2 form [2+2] cycloadducts 3 which are reduced to give alcohols 6. Oxidation of these alcohols at low temperatures leads to unstable aldehydes 7, which either rearrange to dihydropyrans 5 or react with Wittig(‐Horner) reagents to aff...
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| Veröffentlicht in: | Chemische Berichte 1990-09, Vol.123 (9), p.1905-1909 |
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| container_end_page | 1909 |
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| container_issue | 9 |
| container_start_page | 1905 |
| container_title | Chemische Berichte |
| container_volume | 123 |
| creator | Gruseck, Ursula Heuschmann, Manfred |
| description | 2‐Methylen‐1,3‐dioxolane (1) and the methyl acrylates or crotonates 2 form [2+2] cycloadducts 3 which are reduced to give alcohols 6. Oxidation of these alcohols at low temperatures leads to unstable aldehydes 7, which either rearrange to dihydropyrans 5 or react with Wittig(‐Horner) reagents to afford donor‐acceptor‐substituted vinylcyclobutanes 8. The cis‐vinylcyclobutane 8g is prepared by [2+2] cycloaddition of dioxolane 1 and methyl (2E,4Z)‐hexadienoate (9). The configurations and preferred conformations of the vinylcyclobutanes 8 have unequivocally been assigned on the basis of 13C‐and 1H‐NMR spectra. |
| doi_str_mv | 10.1002/cber.19901230924 |
| format | Article |
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Oxidation of these alcohols at low temperatures leads to unstable aldehydes 7, which either rearrange to dihydropyrans 5 or react with Wittig(‐Horner) reagents to afford donor‐acceptor‐substituted vinylcyclobutanes 8. The cis‐vinylcyclobutane 8g is prepared by [2+2] cycloaddition of dioxolane 1 and methyl (2E,4Z)‐hexadienoate (9). The configurations and preferred conformations of the vinylcyclobutanes 8 have unequivocally been assigned on the basis of 13C‐and 1H‐NMR spectra.</description><identifier>ISSN: 0009-2940</identifier><identifier>EISSN: 1099-0682</identifier><identifier>DOI: 10.1002/cber.19901230924</identifier><identifier>CODEN: CHBEAM</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>[2+2] Cycloaddition ; Chemistry ; conformational analysis of ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Vinylcyclobutanes ; Vinylcyclobutanes, conformational analysis of ; Wittig reaction ; Wittig-Horner reaction</subject><ispartof>Chemische Berichte, 1990-09, Vol.123 (9), p.1905-1909</ispartof><rights>Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3634-2323c9c0601f1cd2dd9006a0f8bf046b1ddb2c7f89231b2ae7e3babdaabe4853</citedby><cites>FETCH-LOGICAL-c3634-2323c9c0601f1cd2dd9006a0f8bf046b1ddb2c7f89231b2ae7e3babdaabe4853</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%2Fcber.19901230924$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcber.19901230924$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27931,27932,45581,45582</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19409914$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Gruseck, Ursula</creatorcontrib><creatorcontrib>Heuschmann, Manfred</creatorcontrib><title>Preparation of donor-acceptor-substituted vinylcyclobutanes</title><title>Chemische Berichte</title><addtitle>Chem. Ber</addtitle><description>2‐Methylen‐1,3‐dioxolane (1) and the methyl acrylates or crotonates 2 form [2+2] cycloadducts 3 which are reduced to give alcohols 6. Oxidation of these alcohols at low temperatures leads to unstable aldehydes 7, which either rearrange to dihydropyrans 5 or react with Wittig(‐Horner) reagents to afford donor‐acceptor‐substituted vinylcyclobutanes 8. The cis‐vinylcyclobutane 8g is prepared by [2+2] cycloaddition of dioxolane 1 and methyl (2E,4Z)‐hexadienoate (9). The configurations and preferred conformations of the vinylcyclobutanes 8 have unequivocally been assigned on the basis of 13C‐and 1H‐NMR spectra.</description><subject>[2+2] Cycloaddition</subject><subject>Chemistry</subject><subject>conformational analysis of</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>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Vinylcyclobutanes</subject><subject>Vinylcyclobutanes, conformational analysis of</subject><subject>Wittig reaction</subject><subject>Wittig-Horner reaction</subject><issn>0009-2940</issn><issn>1099-0682</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwM3ZhDJzt1ImFGKBqC6h8CFUwWucvKRCSyE6B_HtaBfExMd0N7_OeniPkkMIxBWAnRrtwTKUEyjhIlm6RAQUpExA52yYDAJAJkynskr0YnwF4mgk-IKf3wTUYsC3qalT7ka2rOiRojGva9RJXOrZFu2qdHb0VVVeazpS1XrVYubhPdjyW0R18zSFZzqbLyWWyuJtfTc4XieGCpwnjjBtpQAD11FhmrQQQCD7XHlKhqbWamcznknGqGbrMcY3aImqX5mM-JNDXmlDHGJxXTSheMXSKgtq4q427-uW-Ro56pMFosPQBK1PEH279BynpJnfW596L0nX_9qrJxfTh752k54vYuo9vHsOLEhnPxurpdq4eZ4sbuJZCUf4JKWt8lQ</recordid><startdate>199009</startdate><enddate>199009</enddate><creator>Gruseck, Ursula</creator><creator>Heuschmann, Manfred</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199009</creationdate><title>Preparation of donor-acceptor-substituted vinylcyclobutanes</title><author>Gruseck, Ursula ; Heuschmann, Manfred</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3634-2323c9c0601f1cd2dd9006a0f8bf046b1ddb2c7f89231b2ae7e3babdaabe4853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>[2+2] Cycloaddition</topic><topic>Chemistry</topic><topic>conformational analysis of</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>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Vinylcyclobutanes</topic><topic>Vinylcyclobutanes, conformational analysis of</topic><topic>Wittig reaction</topic><topic>Wittig-Horner reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gruseck, Ursula</creatorcontrib><creatorcontrib>Heuschmann, Manfred</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemische Berichte</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gruseck, Ursula</au><au>Heuschmann, Manfred</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of donor-acceptor-substituted vinylcyclobutanes</atitle><jtitle>Chemische Berichte</jtitle><addtitle>Chem. Ber</addtitle><date>1990-09</date><risdate>1990</risdate><volume>123</volume><issue>9</issue><spage>1905</spage><epage>1909</epage><pages>1905-1909</pages><issn>0009-2940</issn><eissn>1099-0682</eissn><coden>CHBEAM</coden><abstract>2‐Methylen‐1,3‐dioxolane (1) and the methyl acrylates or crotonates 2 form [2+2] cycloadducts 3 which are reduced to give alcohols 6. Oxidation of these alcohols at low temperatures leads to unstable aldehydes 7, which either rearrange to dihydropyrans 5 or react with Wittig(‐Horner) reagents to afford donor‐acceptor‐substituted vinylcyclobutanes 8. The cis‐vinylcyclobutane 8g is prepared by [2+2] cycloaddition of dioxolane 1 and methyl (2E,4Z)‐hexadienoate (9). The configurations and preferred conformations of the vinylcyclobutanes 8 have unequivocally been assigned on the basis of 13C‐and 1H‐NMR spectra.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/cber.19901230924</doi><tpages>5</tpages></addata></record> |
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| ispartof | Chemische Berichte, 1990-09, Vol.123 (9), p.1905-1909 |
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| language | eng |
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| subjects | [2+2] Cycloaddition Chemistry conformational analysis of Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties Vinylcyclobutanes Vinylcyclobutanes, conformational analysis of Wittig reaction Wittig-Horner reaction |
| title | Preparation of donor-acceptor-substituted vinylcyclobutanes |
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