Synthesis of Medium and Large Ring Compounds, XLIII. Synthesis and Isomerization of 8,9-Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer
An improved sonochemical procedure for the synthesis of dimethyl [6]paracyclophane‐8,9‐dicarboxylate (2a) on a 10‐g scale is described. The title compound 2d was synthesized from 2a in three steps. Irradiation of 2d yielded the Dewar isomer 3. In solution, the reaction enthalpy for the thermal isome...
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| Veröffentlicht in: | Liebigs Annalen 1996-12, Vol.1996 (12), p.1959-1961 |
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| container_end_page | 1961 |
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| container_issue | 12 |
| container_start_page | 1959 |
| container_title | Liebigs Annalen |
| container_volume | 1996 |
| creator | Tochtermann, Werner Rodefeld, Lars Dreeskamp, Herbert Sarge, Stefan M. |
| description | An improved sonochemical procedure for the synthesis of dimethyl [6]paracyclophane‐8,9‐dicarboxylate (2a) on a 10‐g scale is described. The title compound 2d was synthesized from 2a in three steps. Irradiation of 2d yielded the Dewar isomer 3. In solution, the reaction enthalpy for the thermal isomerization of 3 to 2d was determined to be ‐162 ± 16 kJ · mol‐1, while the activation energy for this reaction was found to be 123 ± 12 kJ · mol‐1.
Synthesis of Medium and Large Ring Compounds, XLIII. — Synthesis and Isomerization of 8,9‐Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer |
| doi_str_mv | 10.1002/jlac.199619961203 |
| format | Article |
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Synthesis of Medium and Large Ring Compounds, XLIII. — Synthesis and Isomerization of 8,9‐Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer</description><identifier>ISSN: 0947-3440</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/jlac.199619961203</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation energy ; Calorimetry ; Dewar isomer ; Paracyclophane ; Reaction enthalpy</subject><ispartof>Liebigs Annalen, 1996-12, Vol.1996 (12), p.1959-1961</ispartof><rights>Copyright © 1996 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2543-19845d4b6d285c232a905e6317b711a66fa3c0a09927573d9bf900de6755b23b3</citedby><cites>FETCH-LOGICAL-c2543-19845d4b6d285c232a905e6317b711a66fa3c0a09927573d9bf900de6755b23b3</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%2Fjlac.199619961203$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlac.199619961203$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Tochtermann, Werner</creatorcontrib><creatorcontrib>Rodefeld, Lars</creatorcontrib><creatorcontrib>Dreeskamp, Herbert</creatorcontrib><creatorcontrib>Sarge, Stefan M.</creatorcontrib><title>Synthesis of Medium and Large Ring Compounds, XLIII. Synthesis and Isomerization of 8,9-Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer</title><title>Liebigs Annalen</title><addtitle>Liebigs Ann./Recl</addtitle><description>An improved sonochemical procedure for the synthesis of dimethyl [6]paracyclophane‐8,9‐dicarboxylate (2a) on a 10‐g scale is described. The title compound 2d was synthesized from 2a in three steps. Irradiation of 2d yielded the Dewar isomer 3. In solution, the reaction enthalpy for the thermal isomerization of 3 to 2d was determined to be ‐162 ± 16 kJ · mol‐1, while the activation energy for this reaction was found to be 123 ± 12 kJ · mol‐1.
Synthesis of Medium and Large Ring Compounds, XLIII. — Synthesis and Isomerization of 8,9‐Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer</description><subject>Activation energy</subject><subject>Calorimetry</subject><subject>Dewar isomer</subject><subject>Paracyclophane</subject><subject>Reaction enthalpy</subject><issn>0947-3440</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNqFkN1KwzAUgIMoOH8ewLs8gJ0nTZMuV6Kb00pVcIqCSEibdIv2ZyQVrQ_hM-ucqHjjxeHcnO-D8yG0Q6BPAMK9h1LlfSIE_5wQ6ArqERAiAC5gFfVARHFAowjW0Yb3DwAgOCc99Dbp6nZmvPW4KfCZ0fapwqrWOFVuavClrad42FTz5qnWfhffpkmS9PEPtDhNfFMZZ19Va5t6oRnsimBkK9POuvKO38-VU3mXl818pmqzRFqPD53VU6PxyDwr9yXZQmuFKr3Z_tqb6Hp8dDU8CdKL42R4kAZ5yCIaEDGImI4yrsMBy0MaKgHMcEriLCZEcV4omoP6-D-MWUy1yAoBoA2PGctCmtFNRJbe3DXeO1PIubOVcp0kIBdB5SKo_B30g9lfMs-2NN3_gDxND4Z_DMHSYH1rXr4Nyj1KHtOYyZvzYzkZjyK4HTE5oe_dM4sO</recordid><startdate>199612</startdate><enddate>199612</enddate><creator>Tochtermann, Werner</creator><creator>Rodefeld, Lars</creator><creator>Dreeskamp, Herbert</creator><creator>Sarge, Stefan M.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199612</creationdate><title>Synthesis of Medium and Large Ring Compounds, XLIII. Synthesis and Isomerization of 8,9-Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer</title><author>Tochtermann, Werner ; Rodefeld, Lars ; Dreeskamp, Herbert ; Sarge, Stefan M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2543-19845d4b6d285c232a905e6317b711a66fa3c0a09927573d9bf900de6755b23b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Activation energy</topic><topic>Calorimetry</topic><topic>Dewar isomer</topic><topic>Paracyclophane</topic><topic>Reaction enthalpy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tochtermann, Werner</creatorcontrib><creatorcontrib>Rodefeld, Lars</creatorcontrib><creatorcontrib>Dreeskamp, Herbert</creatorcontrib><creatorcontrib>Sarge, Stefan M.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Liebigs Annalen</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tochtermann, Werner</au><au>Rodefeld, Lars</au><au>Dreeskamp, Herbert</au><au>Sarge, Stefan M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Medium and Large Ring Compounds, XLIII. Synthesis and Isomerization of 8,9-Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer</atitle><jtitle>Liebigs Annalen</jtitle><addtitle>Liebigs Ann./Recl</addtitle><date>1996-12</date><risdate>1996</risdate><volume>1996</volume><issue>12</issue><spage>1959</spage><epage>1961</epage><pages>1959-1961</pages><issn>0947-3440</issn><eissn>1099-0690</eissn><abstract>An improved sonochemical procedure for the synthesis of dimethyl [6]paracyclophane‐8,9‐dicarboxylate (2a) on a 10‐g scale is described. The title compound 2d was synthesized from 2a in three steps. Irradiation of 2d yielded the Dewar isomer 3. In solution, the reaction enthalpy for the thermal isomerization of 3 to 2d was determined to be ‐162 ± 16 kJ · mol‐1, while the activation energy for this reaction was found to be 123 ± 12 kJ · mol‐1.
Synthesis of Medium and Large Ring Compounds, XLIII. — Synthesis and Isomerization of 8,9‐Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/jlac.199619961203</doi><tpages>3</tpages></addata></record> |
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| issn | 0947-3440 1099-0690 |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Activation energy Calorimetry Dewar isomer Paracyclophane Reaction enthalpy |
| title | Synthesis of Medium and Large Ring Compounds, XLIII. Synthesis and Isomerization of 8,9-Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer |
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