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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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231:"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
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43:-alkylated aniline. The reaction requires heat, and the
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In one study this rearrangement was applied to a 3-N(CH
302:at 80 °C gives 30% 2-o (ortho) and 37% 2-p (para)
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204:Berichte der Deutschen Chemischen Gesellschaft
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173:Berichte der Deutschen Chemischen Gesellschaft
117:The reaction is named after German chemists
229:Reilly, J.; Hickinbottom, W. J. (1920).
169:"Methylirung der Phenylgruppe im Anilin"
167:Hofmann, A. W.; Martius, C. A. (1871).
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200:"Umwandlung des Anilins in Toluidin"
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65:Reilly–Hickinbottom rearrangement
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18:Hofmann–Martius rearrangement
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146:Fischer–Hepp rearrangement
123:Carl Alexander von Martius
119:August Wilhelm von Hofmann
80:Fischer–Hepp rearrangement
28:converting an N-alkylated
135:Friedel–Crafts alkylation
88:Friedel–Crafts alkylation
216:10.1002/cber.18720050241
185:10.1002/cber.18710040271
319:Rearrangement reactions
198:Hofmann, A. W. (1872).
26:rearrangement reaction
32:to the corresponding
247:10.1039/ct9201700103
71:and Joseph Reilly).
69:Wilfred Hickinbottom
141:Fries rearrangement
76:Fries rearrangement
84:reaction mechanism
274:10.1021/ol061191z
137:-like reactions:
49:hydrochloric acid
22:organic chemistry
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262:Organic Letters
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268:(16): 3497–9.
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210:(2): 720–722.
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241:: 103–137.
179:(2): 742.
154:References
36:and / or
313:Category
294:heating
282:16869644
129:See also
78:and the
45:catalyst
300:toluene
30:aniline
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82:. Its
34:ortho
24:is a
278:PMID
121:and
41:aryl
38:para
16:The
298:in
270:doi
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101:H
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