Synthesis of cycloproparenes via aromatization of 7-Oxanorbornenes with Low-Valent titanium
1H‐Cyclopropa[b]naphthalene 3c and the 2,7‐diphenyl‐substituted derivative 3a have been synthesized via cycloaddition of the appropriate isobenzofurans 1a and 1b to 1‐bromo‐2‐chlorocyclopropene and aromatization of the adducts with low‐valent Ti. The same procedure afforded the 2,7‐dimethyl‐H‐cyelop...
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| Veröffentlicht in: | Helvetica chimica acta 1989-11, Vol.72 (7), p.1608-1617 |
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| container_title | Helvetica chimica acta |
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| creator | Müller, Paul Schaller, Jean-Pierre |
| description | 1H‐Cyclopropa[b]naphthalene 3c and the 2,7‐diphenyl‐substituted derivative 3a have been synthesized via cycloaddition of the appropriate isobenzofurans 1a and 1b to 1‐bromo‐2‐chlorocyclopropene and aromatization of the adducts with low‐valent Ti. The same procedure afforded the 2,7‐dimethyl‐H‐cyelopropa[g]isoquinoline (15), but failed for the parent azacompound. Reaction of adducts of furans to 1‐bromo‐2‐chlorocyclopropenes with low‐valent Ti produced mixtures of cyclopropabenzenes 19 and 1,6‐dihalogeno‐1,3,5‐cycloheptatrienes 18. The latter could be converted to cyclopropabenzenes with BuLi. |
| doi_str_mv | 10.1002/hlca.19890720721 |
| format | Article |
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The same procedure afforded the 2,7‐dimethyl‐H‐cyelopropa[g]isoquinoline (15), but failed for the parent azacompound. Reaction of adducts of furans to 1‐bromo‐2‐chlorocyclopropenes with low‐valent Ti produced mixtures of cyclopropabenzenes 19 and 1,6‐dihalogeno‐1,3,5‐cycloheptatrienes 18. The latter could be converted to cyclopropabenzenes with BuLi.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.19890720721</identifier><identifier>CODEN: HCACAV</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Helvetica chimica acta, 1989-11, Vol.72 (7), p.1608-1617</ispartof><rights>Copyright © 1989 Verlag GmbH & Co. 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The same procedure afforded the 2,7‐dimethyl‐H‐cyelopropa[g]isoquinoline (15), but failed for the parent azacompound. Reaction of adducts of furans to 1‐bromo‐2‐chlorocyclopropenes with low‐valent Ti produced mixtures of cyclopropabenzenes 19 and 1,6‐dihalogeno‐1,3,5‐cycloheptatrienes 18. The latter could be converted to cyclopropabenzenes with BuLi.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><recordid>eNqFkM1PAjEQxRujiYjePe7B6-q0-9HdgwcCChICxu_ooRlKG6rLlrSrgH-9ixiiJ5OZzOX93ss8Qo4pnFIAdjYtJJ7SPMuBs3roDmnQhLGQpTzZJQ0AmoVA86d9cuD9KwDktbJBXm5XZTVV3vjA6kCuZGHnzs7RqVL54MNggM7OsDKf9dpyLeLhaImldWPrym_VwlTTYGAX4QMWqqyCylRYmvfZIdnTWHh19HOb5P7y4q7dCwej7lW7NQhllMY0ZDwaY4KYxamO2ERTCixlOWgOyCY8jSjnknOIYx0nUo8zlmuFjNfvjVHROGoS2PhKZ713Sou5MzN0K0FBrMsR63LEr3Jq5GSDzNFLLLTDUhq_5VKeQRavnc83soUp1OpfW9EbtFt_Y8INb3ylllse3VsdEfFEPA67osOvb_r9544YRl_6HYcV</recordid><startdate>19891101</startdate><enddate>19891101</enddate><creator>Müller, Paul</creator><creator>Schaller, Jean-Pierre</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19891101</creationdate><title>Synthesis of cycloproparenes via aromatization of 7-Oxanorbornenes with Low-Valent titanium</title><author>Müller, Paul ; Schaller, Jean-Pierre</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3641-273ba5aa846f32df11026290f70a2d763177c77044f45cfb829fea27152bae143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Müller, Paul</creatorcontrib><creatorcontrib>Schaller, Jean-Pierre</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Müller, Paul</au><au>Schaller, Jean-Pierre</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of cycloproparenes via aromatization of 7-Oxanorbornenes with Low-Valent titanium</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>1989-11-01</date><risdate>1989</risdate><volume>72</volume><issue>7</issue><spage>1608</spage><epage>1617</epage><pages>1608-1617</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><coden>HCACAV</coden><abstract>1H‐Cyclopropa[b]naphthalene 3c and the 2,7‐diphenyl‐substituted derivative 3a have been synthesized via cycloaddition of the appropriate isobenzofurans 1a and 1b to 1‐bromo‐2‐chlorocyclopropene and aromatization of the adducts with low‐valent Ti. The same procedure afforded the 2,7‐dimethyl‐H‐cyelopropa[g]isoquinoline (15), but failed for the parent azacompound. Reaction of adducts of furans to 1‐bromo‐2‐chlorocyclopropenes with low‐valent Ti produced mixtures of cyclopropabenzenes 19 and 1,6‐dihalogeno‐1,3,5‐cycloheptatrienes 18. The latter could be converted to cyclopropabenzenes with BuLi.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/hlca.19890720721</doi><tpages>10</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Synthesis of cycloproparenes via aromatization of 7-Oxanorbornenes with Low-Valent titanium |
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