Properties, Preparation and Synthetic Uses of Amine<i>N</i>-Oxides. An Update

Bernier, David; Wefelscheid, Ulrike K.; Woodward, Simon

doi:10.1080/00304940902955756

Cited by 60 publications

(60 citation statements)

References 132 publications

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“…It has been previously reported that isocyanides are known to polymerize on gold surfaces. 18,19 Since GC analysis of the reaction solutions showed no new products, we analyzed the gold powder surface for isocyanide polymers by diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS). Earlier, McCarley had observed a broad band centered at 1640 cm -1 , 19 which was assigned to adsorbed polyisocyanide, which was formed when 1,6-diisocyanohexane (DICH) was adsorbed on a gold film.…”

Section: Resultsmentioning

confidence: 99%

“…18,19 Since GC analysis of the reaction solutions showed no new products, we analyzed the gold powder surface for isocyanide polymers by diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS). Earlier, McCarley had observed a broad band centered at 1640 cm -1 , 19 which was assigned to adsorbed polyisocyanide, which was formed when 1,6-diisocyanohexane (DICH) was adsorbed on a gold film. Likewise, the adsorption of DICH on a Cu film resulted in a broad peak, attributed to the N=C double bond of the adsorbed polyisocyanide, at 1650 cm -1 .…”

Section: Resultsmentioning

confidence: 99%

“…An increase of at least 40 cm -1 , which is a general benchmark, indicates that both the isocyanide adsorbed on the gold surface and the isocyanide ligand in the metal complexes have a high susceptibility to undergo reaction with nucleophiles. 19 …”

Section: Adsorption Of Isocyanides On Gold Surfacesmentioning

confidence: 99%

“…Kinetic studies indicated that the reaction was first order in the amine concentration and zero order in the oxygen concentration. 19 The first step of the reaction involves isocyanide adsorption to the metal surface (η 1 rate-determining amine attack on the adsorbed isocyanide, the steric and electronic effects of the amine significantly influenced the rate of reaction.…”

Section: Reactions Of Isocyanides Adsorbed On Gold Surfacesmentioning

confidence: 99%

“…In this case, isocyanides and primary amines were converted to carbodiimides in the presence of air. 19 This reaction was then investigated using gold powder as a catalyst, with oxygen (~1 L, ~1 atm) and various primary amine concentrations at room temperature. Kinetic studies indicated that the reaction was first order in the amine concentration and zero order in the oxygen concentration.…”

Section: Reactions Of Isocyanides Adsorbed On Gold Surfacesmentioning

confidence: 99%

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Bulk gold catalyzed oxidation reactions of amines and isocyanides and iron porphyrin catalyzed N-H and O-H bond insertion/cyclization reactions of diamines and aminoalcohols

Klobukowski

2011

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Adsorption Of Isocyanides On Gold Surfacesmentioning

confidence: 99%

Section: Reactions Of Isocyanides Adsorbed On Gold Surfacesmentioning

confidence: 99%

Section: Reactions Of Isocyanides Adsorbed On Gold Surfacesmentioning

confidence: 99%

See 3 more Smart Citations

Bulk gold catalyzed oxidation reactions of amines and isocyanides and iron porphyrin catalyzed N-H and O-H bond insertion/cyclization reactions of diamines and aminoalcohols

Klobukowski

2011

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Surface Grafted N‐Oxides have Low‐Fouling and Antibacterial Properties

Burmeister,

Zorn,

Farooq

et al. 2023

Adv Materials Inter

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Low‐fouling materials are often generated by surface zwitterionization with polymers. In this context, poly‐N‐oxides have recently attracted considerable attention as biomimetic stealth coatings with low protein adsorption. Herein, this study reports that poly‐N‐oxides can be grafted from plasma‐activated plastic base materials. The resulting hydrophilic surfaces have low‐fouling properties in bacterial suspensions and suppress the formation of biofilms. Moreover, efficient antibacterial activity against Gram‐negative and Gram‐positive bacteria caused by release of reactive oxygen species is observed. The latter effect is specific for polymeric N‐oxides and is most likely triggered by a reductive activation of the N‐oxide functionality in the presence of bacteria. In contrast to other zwitterionic polymers, N‐oxides combine thus low‐fouling (stealth) properties with antibacterial activity. The bioactive N‐oxide groups can be regenerated after use by common oxidative disinfectants. Poly‐N‐oxides are thus attractive antibacterial coatings for many base materials with a unique combined mechanism of action.

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Asymmetric Oxidative Mannich Reactions

et al. 2020

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The asymmetric Mannich reaction is one of the most straightforward methodologies for the enantioselective synthesis of chiral amines. In general, asymmetric Mannich reactions involve the use of imines as electrophiles. However, in recent years, several asymmetric oxidative Mannich reactions have been reported using amines as electrophiles. This review provides an overview of these recent publications, including the different oxidants used and the scope and limitations of the different catalytic systems.

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Properties, Preparation and Synthetic Uses of AmineN-Oxides. An Update

Cited by 60 publications

References 132 publications

Bulk gold catalyzed oxidation reactions of amines and isocyanides and iron porphyrin catalyzed N-H and O-H bond insertion/cyclization reactions of diamines and aminoalcohols

Bulk gold catalyzed oxidation reactions of amines and isocyanides and iron porphyrin catalyzed N-H and O-H bond insertion/cyclization reactions of diamines and aminoalcohols

Surface Grafted N‐Oxides have Low‐Fouling and Antibacterial Properties

Asymmetric Oxidative Mannich Reactions

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