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Magnus, Philip; Turnbull, Rachel (2006). "Thermal and Acid-Catalyzed
Hofmann–Martius Rearrangement of 3-N-Aryl-2-oxindoles into 3-(Arylamino)-2-oxindoles".
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centers around dissociation of the reactant with the positively charged organic residue R attacking the aniline ring in a
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The reaction is also known to work for aryl ethers and two conceptually related reactions are the
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242:"XV.—Intramolecular rearrangement of the alkylarylamines: Formation of 4-amino-n-butylbenzene"
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When the catalyst is a metal halide the reaction is also called the
54:-alkylated aniline. The reaction requires heat, and the
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In one study this rearrangement was applied to a 3-N(CH
313:at 80 °C gives 30% 2-o (ortho) and 37% 2-p (para)
215:Berichte der Deutschen Chemischen Gesellschaft
184:Berichte der Deutschen Chemischen Gesellschaft
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128:The reaction is named after German chemists
240:Reilly, J.; Hickinbottom, W. J. (1920).
180:"Methylirung der Phenylgruppe im Anilin"
178:Hofmann, A. W.; Martius, C. A. (1871).
170:
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211:"Umwandlung des Anilins in Toluidin"
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76:Reilly–Hickinbottom rearrangement
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29:Hofmann–Martius rearrangement
18:Hofmann-Martius rearrangement
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157:Fischer–Hepp rearrangement
134:Carl Alexander von Martius
130:August Wilhelm von Hofmann
91:Fischer–Hepp rearrangement
39:converting an N-alkylated
146:Friedel–Crafts alkylation
99:Friedel–Crafts alkylation
227:10.1002/cber.18720050241
196:10.1002/cber.18710040271
330:Rearrangement reactions
209:Hofmann, A. W. (1872).
37:rearrangement reaction
43:to the corresponding
258:10.1039/ct9201700103
82:and Joseph Reilly).
80:Wilfred Hickinbottom
152:Fries rearrangement
87:Fries rearrangement
95:reaction mechanism
285:10.1021/ol061191z
148:-like reactions:
60:hydrochloric acid
33:organic chemistry
16:(Redirected from
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273:Organic Letters
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279:(16): 3497–9.
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116:)-2-oxindole:
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252:: 103–137.
190:(2): 742.
165:References
47:and / or
324:Category
305:heating
293:16869644
140:See also
89:and the
56:catalyst
311:toluene
41:aniline
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93:. Its
45:ortho
35:is a
289:PMID
132:and
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49:para
27:The
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