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215:, they form the same anion upon deprotonation. The two names are thus synonyms describing the same anion, although arguably, imidate refers to the resonance contributor on the left, while amidate refers to the resonance contributor on the right. However, they are distinguished when they act as ligands for transition metals, with
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Imidates produced in this manner are formed as their hydrochloride salts, which are sometimes referred to as Pinner salts. Carboximidates are also formed as intermediates in the
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298:-arylbenzimidates to the corresponding amides, via intramolecular migration of an aryl group from oxygen to nitrogen. It is named after
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Yu, Biao; Yu, Hai; Hui, Yongzheng; Han, Xiuwen (June 1999). "Trichloroacetimidate as an
Efficient Protective Group for Alcohols".
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Chapman, Arthur
William (1925). "CCLXIX.—Imino-aryl ethers. Part III. The molecular rearrangement of
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223:-bound species referred to as amidates. They can be considered aza-substituted analogues of
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Imidates may be generated by a number of synthetic routes, but are in general formed by the
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156:(>C=N-) with an oxygen atom connected to the carbon atom of the C=N double bond.
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and by an analogous process react with amines (including ammonia) to form
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Roger, Robert; Neilson, Douglas G. (1961). "The
Chemistry of Imidates".
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168:. This proceeds via the acid catalyzed attack of nitriles by alcohols.
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Schulenberg, J. W.; Archer, S. (1965). "The
Chapman Rearrangement".
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275:, aromatic imidates can also be converted but far less readily.
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302:, who first described it, and is conceptually similar to the
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for alcohols. For example, the base catalyzed reaction of
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378: — the corresponding 5-membered heterocycle
133:) are organic compounds, which can be thought of as
552:(4th ed.). Hoboken, N.J.: WILEY. p. 244.
350:protections and may be cleaved by acid hydrolysis.
46:. Unsourced material may be challenged and removed.
454:Name Reactions and Reagents in organic Synthesis
247:and undergo a range of addition reactions; with
548:Wuts, Peter G. M.; Greene, Theodora W. (2006).
456:, 2. Auflage, Wiley-Interscience, Hoboken, NJ
8:
452:B. P. Mundy, M. G. Ellerd, F. G. Favaloro:
219:bound species referred to as imidates and
372: — the "acyl chloride" variant
145:, with the general formula R-C(=NR')OR".
106:Learn how and when to remove this message
251:imidates generally reacting faster than
175:General mechanism of the Pinner reaction
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550:Protective groups in organic synthesis
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211:. Since amides and imidic acids are
44:adding citations to reliable sources
294:is the thermal conversion of aryl
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521:-phenylbenziminophenyl ether".
31:needs additional citations for
1:
326:Benzyl trichloroethanimidate
227:with the formula R-N=C(O)R.
494:10.1002/0471264180.or014.01
403:. Buckten, CH: Reto Mueller
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330:Carboximidates can act as
304:Newman–Kwart rearrangement
234:Imidate/amidate resonance
401:Organic Chemistry Portal
243:Carboximidates are good
148:They are also known as
122:The carboximidate group
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300:Arthur William Chapman
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255:imidates. They can be
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191:Imidate/amidate anions
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152:, since they resemble
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340:trichloroacetonitrile
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318:As a protecting group
313:Chapman Rearrangement
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292:Chapman rearrangement
286:Chapman rearrangement
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199:anion is formed upon
185:Overman rearrangement
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141:(R-C(=NR')OH) and an
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535:10.1039/CT9252701992
523:J. Chem. Soc., Trans
344:trichloroacetimidate
40:improve this article
587:10.1055/s-1999-2736
440:10.1021/cr60210a003
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181:Mumm rearrangement
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612:Functional groups
559:978-0-471-69754-1
481:Organic Reactions
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397:"Pinner Reaction"
137:formed between a
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405:. Retrieved
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150:imino ethers
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38:Please help
33:verification
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269:orthoesters
209:imidic acid
139:imidic acid
96:August 2022
601:Categories
503:0471264180
407:2023-09-26
383:References
257:hydrolyzed
66:newspapers
468:, S. 516.
376:Oxazoline
342:yields a
249:aliphatic
239:Reactions
213:tautomers
160:Synthesis
488:: 1–51.
360:Amidines
354:See also
265:amidines
259:to give
253:aromatic
225:enolates
183:and the
131:imidates
575:Synlett
143:alcohol
80:scholar
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365:Esters
271:RC(OR)
261:esters
203:of an
154:imines
135:esters
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338:upon
205:amide
87:JSTOR
73:books
579:1999
554:ISBN
498:ISBN
462:ISBN
458:2005
290:The
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348:TBS
207:or
195:An
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217:O-
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519:N
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273:3
221:N
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