| http://dbpedia.org/ontology/abstract
|
The Scholl reaction is a coupling reaction … The Scholl reaction is a coupling reaction between two arene compounds with the aid of a Lewis acid and a protic acid. It is named after its discoverer, Roland Scholl, a Swiss chemist. In 1910 Scholl reported the synthesis of a quinone and of perylene from naphthalene both with aluminum chloride. Perylene was also synthesised from 1,1’-binaphthalene in 1913. The synthesis of Benzanthrone was reported in 1912. The protic acid in the Scholl reaction is often an impurity in the Lewis Acid and also formed in the course of a Scholl reaction. Reagents are iron(III) chloride in dichloromethane, copper(II) chloride, PIFA and boron trifluoride etherate in dichloromethane, Molybdenum(V) chloride and lead tetraacetate with BF3 in acetonitrile. Given the high reaction temperature and the requirement for strongly acidic catalysts the chemical yield often is low and the method is not a popular one. Intramolecular reactions fare better than the intermolecular ones, for instance in the organic synthesis of 9-phenylfluorene: Or the formation of the pyrene dibenzo-(a.1)-pyrene from the anthracene 1-phenylbenz(a)anthracene (66% yield). One study showed that the reaction lends itself to cascade reactions to form more complex polycyclic aromatic hydrocarbons In certain applications such as triphenylene synthesis this reaction is advocated as an alternative for the Suzuki reaction. A recurring problem is oligomerization of the product which can be prevented by blocking tert-butyl substituents:ented by blocking tert-butyl substituents:
, 朔尔反应（德語：Scholl-Reaktion）指两分子芳烃在路易斯酸和质子酸存在下偶联为联芳烃。 常用的反应试剂有氯化铁-二氯甲烷；氯化铜、(双(三氟乙酰氧基)碘)苯和三氟化硼醚络合物在二氯甲烷中的溶液，以及五氯化钼和四乙酸铅与三氟化硼在乙腈中的溶液。 反应所需温度较高，亦需要强酸性催化剂，因此反应产率一般较低，应用很少。分子内的朔尔反应效果较分子间反应效果为好，例如下图中9-苯基芴的制取： 以及从1-苯基苯并蒽的环化制取二苯并-(a.1)-芘（产率66%）：
, De Scholl-reactie (genoemd naar de ontdekk … De Scholl-reactie (genoemd naar de ontdekker, ) is een methode om twee aromaten met elkaar te koppelen met behulp van een lewiszuur en een protisch zuur: Gezien de temperatuur waarbij de reactie moet doorgaan hoog is en er sterke zure katalysatoren moeten gebruikt worden, zijn de opbrengsten meestal aan de lage kant waardoor de methode een lage populariteit geniet. Intramoleculaire reacties gaan wel beter op dan , bijvoorbeeld de synthese van : Of de vorming van dibenzo-(a.1)-pyreen vanuit 1-fenylbenz(a)anthraceen (66% rendement): Het exacte reactiemechanisme is niet bekend, maar zou via een kunnen verlopen. bekend, maar zou via een kunnen verlopen.
, Die Scholl-Reaktion ist eine Namensreaktion aus dem Bereich der organischen Chemie und wurde erstmals 1910 von Roland Scholl (1865–1945) beobachtet. Dabei findet eine Kupplung von Aromaten statt.
|
| http://dbpedia.org/ontology/thumbnail
|
http://commons.wikimedia.org/wiki/Special:FilePath/Scholl-reactie.png?width=300 +
|
| http://dbpedia.org/ontology/wikiPageID
|
5533592
|
| http://dbpedia.org/ontology/wikiPageLength
|
5622
|
| http://dbpedia.org/ontology/wikiPageRevisionID
|
1118574773
|
| http://dbpedia.org/ontology/wikiPageWikiLink
|
http://dbpedia.org/resource/File:Schollvb2.png +
, http://dbpedia.org/resource/Arene_compound +
, http://dbpedia.org/resource/File:SchollreactionBlockingSubstituents.png +
, http://dbpedia.org/resource/File:Schollvb.png +
, http://dbpedia.org/resource/File:Scholl-reactie.png +
, http://dbpedia.org/resource/Arenium_ion +
, http://dbpedia.org/resource/File:SchollReactionParadirectors.png +
, http://dbpedia.org/resource/Phenyliodine_bis%28trifluoroacetate%29 +
, http://dbpedia.org/resource/Coupling_reaction +
, http://dbpedia.org/resource/Benzanthrone +
, http://dbpedia.org/resource/Activating_group +
, http://dbpedia.org/resource/Suzuki_reaction +
, http://dbpedia.org/resource/Perylene +
, http://dbpedia.org/resource/Naphthalene +
, http://dbpedia.org/resource/Dichloromethane +
, http://dbpedia.org/resource/Anthracene +
, http://dbpedia.org/resource/Pyrene +
, http://dbpedia.org/resource/Organic_synthesis +
, http://dbpedia.org/resource/Fluorene +
, http://dbpedia.org/resource/Polycyclic_aromatic_hydrocarbon +
, http://dbpedia.org/resource/Reaction_mechanism +
, http://dbpedia.org/resource/Electrophilic_aromatic_substitution +
, http://dbpedia.org/resource/Boron_trifluoride +
, http://dbpedia.org/resource/Aromatization +
, http://dbpedia.org/resource/Molybdenum%28V%29_chloride +
, http://dbpedia.org/resource/Iron%28III%29_chloride +
, http://dbpedia.org/resource/Catalyst +
, http://dbpedia.org/resource/Category:Name_reactions +
, http://dbpedia.org/resource/Lewis_acid +
, http://dbpedia.org/resource/Methoxy +
, http://dbpedia.org/resource/Cascade_reaction +
, http://dbpedia.org/resource/Copper%28II%29_chloride +
, http://dbpedia.org/resource/Roland_Scholl +
, http://dbpedia.org/resource/Lead_tetraacetate +
, http://dbpedia.org/resource/Oligomerization +
, http://dbpedia.org/resource/Tert-butyl +
, http://dbpedia.org/resource/Category:Substitution_reactions +
, http://dbpedia.org/resource/Aluminum_chloride +
, http://dbpedia.org/resource/Triphenylene +
, http://dbpedia.org/resource/Acetonitrile +
, http://dbpedia.org/resource/Friedel-Crafts_alkylation +
, http://dbpedia.org/resource/Protic_acid +
, http://dbpedia.org/resource/Chemical_yield +
, http://dbpedia.org/resource/Radical_cation +
, http://dbpedia.org/resource/Intramolecular_reaction +
|
| http://dbpedia.org/property/name
|
Scholl reaction
|
| http://dbpedia.org/property/namedafter
|
http://dbpedia.org/resource/Roland_Scholl +
|
| http://dbpedia.org/property/type
|
Coupling reaction
|
| http://dbpedia.org/property/wikiPageUsesTemplate
|
http://dbpedia.org/resource/Template:Reflist +
, http://dbpedia.org/resource/Template:Reactionbox +
, http://dbpedia.org/resource/Template:Reactionbox_Identifiers +
|
| http://purl.org/dc/terms/subject
|
http://dbpedia.org/resource/Category:Name_reactions +
, http://dbpedia.org/resource/Category:Substitution_reactions +
|
| http://purl.org/linguistics/gold/hypernym
|
http://dbpedia.org/resource/Reaction +
|
| http://www.w3.org/ns/prov#wasDerivedFrom
|
http://en.wikipedia.org/wiki/Scholl_reaction?oldid=1118574773&ns=0 +
|
| http://xmlns.com/foaf/0.1/depiction
|
http://commons.wikimedia.org/wiki/Special:FilePath/SchollreactionBlockingSubstituents.png +
, http://commons.wikimedia.org/wiki/Special:FilePath/Schollvb.png +
, http://commons.wikimedia.org/wiki/Special:FilePath/Schollvb2.png +
, http://commons.wikimedia.org/wiki/Special:FilePath/Scholl-reactie.png +
, http://commons.wikimedia.org/wiki/Special:FilePath/SchollReactionParadirectors.png +
|
| http://xmlns.com/foaf/0.1/isPrimaryTopicOf
|
http://en.wikipedia.org/wiki/Scholl_reaction +
|
| owl:sameAs |
http://www.wikidata.org/entity/Q2453366 +
, http://sl.dbpedia.org/resource/Schollova_reakcija +
, http://dbpedia.org/resource/Scholl_reaction +
, http://de.dbpedia.org/resource/Scholl-Reaktion +
, http://yago-knowledge.org/resource/Scholl_reaction +
, http://zh.dbpedia.org/resource/%E6%9C%94%E5%B0%94%E5%8F%8D%E5%BA%94 +
, http://fa.dbpedia.org/resource/%D9%88%D8%A7%DA%A9%D9%86%D8%B4_%D8%B4%D9%88%D9%84 +
, http://nl.dbpedia.org/resource/Scholl-reactie +
, https://global.dbpedia.org/id/2JjWg +
, http://rdf.freebase.com/ns/m.0dr8zb +
|
| rdf:type |
http://dbpedia.org/ontology/Disease +
, http://dbpedia.org/class/yago/WikicatNameReactions +
, http://dbpedia.org/class/yago/PhysicalEntity100001930 +
, http://dbpedia.org/class/yago/ChemicalReaction113447361 +
, http://dbpedia.org/class/yago/ChemicalProcess113446390 +
, http://dbpedia.org/class/yago/Process100029677 +
, http://dbpedia.org/class/yago/WikicatSubstitutionReactions +
, http://dbpedia.org/class/yago/NaturalProcess113518963 +
|
| rdfs:comment |
De Scholl-reactie (genoemd naar de ontdekk … De Scholl-reactie (genoemd naar de ontdekker, ) is een methode om twee aromaten met elkaar te koppelen met behulp van een lewiszuur en een protisch zuur: Gezien de temperatuur waarbij de reactie moet doorgaan hoog is en er sterke zure katalysatoren moeten gebruikt worden, zijn de opbrengsten meestal aan de lage kant waardoor de methode een lage populariteit geniet. Intramoleculaire reacties gaan wel beter op dan , bijvoorbeeld de synthese van : Of de vorming van dibenzo-(a.1)-pyreen vanuit 1-fenylbenz(a)anthraceen (66% rendement): 1-fenylbenz(a)anthraceen (66% rendement):
, 朔尔反应（德語：Scholl-Reaktion）指两分子芳烃在路易斯酸和质子酸存在下偶联为联芳烃。 常用的反应试剂有氯化铁-二氯甲烷；氯化铜、(双(三氟乙酰氧基)碘)苯和三氟化硼醚络合物在二氯甲烷中的溶液，以及五氯化钼和四乙酸铅与三氟化硼在乙腈中的溶液。 反应所需温度较高，亦需要强酸性催化剂，因此反应产率一般较低，应用很少。分子内的朔尔反应效果较分子间反应效果为好，例如下图中9-苯基芴的制取： 以及从1-苯基苯并蒽的环化制取二苯并-(a.1)-芘（产率66%）：
, Die Scholl-Reaktion ist eine Namensreaktion aus dem Bereich der organischen Chemie und wurde erstmals 1910 von Roland Scholl (1865–1945) beobachtet. Dabei findet eine Kupplung von Aromaten statt.
, The Scholl reaction is a coupling reaction … The Scholl reaction is a coupling reaction between two arene compounds with the aid of a Lewis acid and a protic acid. It is named after its discoverer, Roland Scholl, a Swiss chemist. In 1910 Scholl reported the synthesis of a quinone and of perylene from naphthalene both with aluminum chloride. Perylene was also synthesised from 1,1’-binaphthalene in 1913. The synthesis of Benzanthrone was reported in 1912. Or the formation of the pyrene dibenzo-(a.1)-pyrene from the anthracene 1-phenylbenz(a)anthracene (66% yield).ene 1-phenylbenz(a)anthracene (66% yield).
|
| rdfs:label |
Scholl-Reaktion
, 朔尔反应
, Scholl-reactie
, Scholl reaction
|
