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are also feasible. This reaction does not take place in a single step but leads first to dihydropentacene that is dehydrogenated in a second step with
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The Elbs reaction enables the synthesis of condensed aromatic systems. As already demonstrated by Elbs in 1884 it is possible to obtain
54:. The reaction was published in 1884. Elbs however did not correctly interpret the reaction product due to a lack of knowledge about
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G. M. Badger, B. J. Christie. (1956). "Polynuclear heterocyclic systems. Part X. The elbs reaction with heterocyclic ketones."
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The Elbs reaction is sometimes accompanied by elimination of substituents and can be unsuited for substituted polyaromatics.
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At least three plausible mechanisms for the Elbs reaction have been suggested. The first mechanism, suggested by
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Alternatively, in the second mechanism, due to Cook, the methylated aromatic compound instead first undergoes a
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to give the same intermediate, which then similarly undergoes a -hydride shift and dehydration.
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derivative was published. The expected linear product was not obtained due to a change in
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Organische Chemie: Grundlagen, Stoffklassen, Reaktionen, Konzepte, Molekülstrukturen
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after formation of the first intermediate which caused multiple
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compounds required for this reaction can be obtained through a
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216:, Einar Larsen. (1884). "Ueber Paraxylylphenylketon."
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via the Elbs reaction. In 1956 an Elbs reaction of a
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A third mechanism has also been proposed, involving
339:Comprehensive Organic Name Reactions and Reagents
276:Fieser, Louis F. (1942). "The Elbs Reaction."
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306:Eberhard Breitmaier, Günther Jung (2005).
89:Elbs reaction to anthracite and pentacene
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124:of the benzophenone, followed by a
174:It is also possible to synthesise
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132:then affords the polyaromatic.
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120:, begins with a heat-induced
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50:, also responsible for the
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341:. 2010. pp. 982–985.
312:(5th edition). Stuttgart:
197:Heterocyclic Elbs reaction
232:10.1002/cber.188401702247
128:to give the compound . A
265:10.1002/prac.18860330119
99:Friedel-Crafts acylation
219:Ber. Dtsch. Chem. Ges.
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176:heterocyclic compounds
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149:electrocyclic reaction
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384:10.1039/JR9560003435
166:radical generation.
130:dehydration reaction
314:Georg Thieme Verlag
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184:reaction mechanism
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139:Fieser's mechanism
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402:Organic reactions
337:"Elbs Reaction".
322:978-3-13-541505-5
103:aluminum chloride
16:Chemical reaction
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147:followed by an
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82:as a catalyst.
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42:to a condensed
27:describing the
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126:-hydride shift
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52:Elbs oxidation
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188:free radical
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44:polyaromatic
40:benzophenone
38:substituted
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286:: 129-154,
279:Org. React.
122:cyclisation
72:dehydration
58:structure.
56:naphthalene
396:Categories
202:References
170:Variations
68:anthracene
214:Karl Elbs
180:thiophene
164:pyrolytic
112:Mechanism
76:pentacene
48:Karl Elbs
29:pyrolysis
70:through
247:K. Elbs
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320:
118:Fieser
80:copper
36:methyl
31:of an
23:is an
101:with
62:Scope
33:ortho
376:1956
351:ISBN
318:ISBN
95:acyl
93:The
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