The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience

Colombo, María Isabel; Bohn, Marı́a L.; Rúveda, Edmundo A.

doi:10.1021/ed079p484

Cited by 15 publications

(7 citation statements)

References 7 publications

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“…Replacing part of the organic solvent having labile C−H bonds with water was beneficial for the process. Oxidation of II , by a SET reaction has been reported as feasible and we propose that methanesulfonyl radical acts here as oxidant in the formation of the nitrilium ion III responsible for the formation of the desired benzamides 2 – 4 upon water addition (paths d, e) …”

Section: Methodsmentioning

confidence: 94%

A Visible‐Light‐Driven, Metal‐free Route to Aromatic Amides via Radical Arylation of Isonitriles

2017

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Section: Methodsmentioning

confidence: 94%

A Visible‐Light‐Driven, Metal‐free Route to Aromatic Amides via Radical Arylation of Isonitriles

2017

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“…The structure of all new compounds was confirmed by elemental analysis and/or accurate mass measurement, IR, 1 H NMR, 13 C NMR, and mass spectral data. The amines were fully characterized as their corresponding hydrochloride or tartrate salts.…”

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confidence: 82%

“…Hydrolysis of these amides should lead to the expected 2,2-dialkylamantadine derivatives ( 7 ) (Scheme ). Interestingly, although the combination of a Ritter reaction with a Wagner–Meerwein rearrangement has been used for mechanistic studies, , its combination for synthetic purposes has been very limited. − …”

mentioning

confidence: 99%

Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds

Torres

Fernández

Miquet

et al. 2012

ACS Med. Chem. Lett.

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The synthesis of several 2,2-dialkyladamantyl-1-amines through the combination of a Ritter reaction with a Wagner−Meerwein rearrangement from noradamantane alcohols is reported. Several of the novel amines displayed low micromolar activities against several H1N1 influenza virus strains, including the amantadine-resistant A/PuertoRico/8/34 strain. Most of the compounds did not show cytotoxicity for MDCK cells.

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“…Proclivity of carbocation rearrangement in the Ritter reaction has been reported in the literature; however, amidated products have still been isolated on small‐molecule substrates – . Christol and coworkers published a large body of work on the application of the Ritter reaction, including a thorough investigation of the effect of solvent conditions and acid strength on the acid catalyzed carbocation rearrangement of a variety of substrates – .…”

Section: Resultsmentioning

confidence: 99%

Functionalization of polyisobutylene and polyisobutylene oligomers via the ritter reaction

Parada

Storey

2018

J. Polym. Sci. Part A: Polym. Chem.

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The Ritter reaction, that is, reaction of a carbocation with a nitrile, was carried out on polyisobutylene (PIB) using a variety of reaction conditions. End quenching of PIB carbocations with acrylonitrile under living polymerization conditions (methyl chloride (MeCl)/hexane 60/40 (v/v) solvent mixtures at 270 8C) resulted in either tert-chloride end groups or loss of chain-end fidelity via carbocation rearrangement, as evidenced by NMR spectroscopy. Exo-olefin functionalized PIB substrates were also reacted with nitriles under a variety of reaction conditions including various acid and solvent medium combinations. In all cases, the result was either no reaction or PIB that had undergone severe backbone degradation, as determined via NMR spectroscopy and gel permeation chromatography. Finally, the Ritter reaction was performed on a series of exo-olefin functionalized oligoisobutylenes using acrylonitrile as the nitrile and either 60/40 dichloromethane/hexane or excess acrylonitrile as the solvent. In 60/40 dichloromethane/hexane, significant carbocation rearrangement and/or degradation resulted in a variety of isomeric, acrylamide-functionalized oligomers. In excess acrylonitrile, the desired Ritter reaction was the only reaction observed, resulting in the smooth formation of the terminal acrylamide. The various N-oligoisobutylacrylamides thus obtained represent new hydrophobic monomers useful for the introduction of hydrophobic moieties into acrylamide-based water-soluble polymers.

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The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience

Cited by 15 publications

References 7 publications

A Visible‐Light‐Driven, Metal‐free Route to Aromatic Amides via Radical Arylation of Isonitriles

A Visible‐Light‐Driven, Metal‐free Route to Aromatic Amides via Radical Arylation of Isonitriles

Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds

Functionalization of polyisobutylene and polyisobutylene oligomers via the ritter reaction

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