Sulfamic Acid and Its N- and O-Substituted Derivatives

Anomeric amides — Structure, properties and reactivity

A novel and reusable ionically tagged nanomagnetic catalyst: Application for the preparation of 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-arylnicotinonitriles via vinylogous anomeric based oxidation

Bisheteroatom-substituted amides (R–CO–NXY) can undergo a novel rearrangement of the more electronegative atom from nitrogen to the carbonyl carbon producing acyl derivatives (R–CO–X) and substituted nitrenes (N–Y). Such reactions have been observed chemically. AM1 molecular orbital calculations on N-substituted acetamides support the concerted nature of this process and predict that amino substituents (Y = NR2) promote the rearrangement of similarly or more electronegative nitrogen substituents (X = NR2, Cl, OR). Migration appears to be driven by an anomeric effect involving interaction between the lone pair on Y and the X–N σ* orbital. Favourable transiton states display a significant increase in N–Y double bond character, negative charge on the migrating substituent and little RCO–N heterolysis. 6–31G*ab initio calculations on migration of the hydroxy group in N-amino-N-hydroxyformamide largely accord with the AM1 findings for this model compound.

Molecular orbital studies of novel N to C migrations in N,N-bisheteroatom-substituted amides—HERON rearrangements

Correction for ‘The first computational study for the oxidative aromatization of pyrazolines and 1,4-dihydropyridines using 1,2,4-triazolinediones: an anomeric-based oxidation’ by Mahya Kiafar et al., RSC Adv., 2016, 6, 102280–102291.

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Correction: The first computational study for the oxidative aromatization of pyrazolines and 1,4-dihydropyridines using 1,2,4-triazolinediones: an anomeric-based oxidation

1.

N-Chloro-N-alkoxysulfonamides and N-chloro-N-alkoxyphosphoamides have chlorinating properties in the reaction with triethylamine in methanol.




2.

N-Chloro-N-alkoxyureas were synthesized for the first time, and from them previously unknown N,N-dialkoxyureas were obtained by nucleophilic substitution reactions.

Geminal systems. Communication 28 Alcoholysis of N-chloro-N-alkoxyamides and synthesis of N,N-dialkoxyureas

In the reaction of N-chloro-N-methoxy-N′,N′-dimethylurea with amines, a nucleophilic substitution of the chlorine atom at the N atom takes place to form N-alkoxyhydrazines, which are stable in the reaction with Me3N, pyridine, toluenesulfonamides, and give products of further transformations with Me2NH and MeONHMe.

Geminal systems. Communication 29. Reactions of N-chloro-N-methoxy-N′,N′-dimethylurea with N-nucleophiles

Certain examples of difluoroamine alkylation reactions

A method was developed for the preparation of the 2,2-difluoro-2-nitroethyl ethers of 1,2-alkylene glycols by reacting 2,2-difluoro-2-nitroethanol with the appropriate olefin α-oxides.

V. I. Shevchenko

Papers

Geminal systems. Communication 28 Alcoholysis of N-chloro-N-alkoxyamides and synthesis of N,N-dialkoxyureas

Geminal systems. Communication 29. Reactions of N-chloro-N-methoxy-N′,N′-dimethylurea with N-nucleophiles

Certain examples of difluoroamine alkylation reactions

Difluoronitroethyl ethers of 1,2-alkylene glycols and their derivatives

2-Dimethylcarbamoyl-1,3,2-dioxazolidine, 2-dimethylcarbamoyl- and 2h-perhydro-1,3,2-dioxazines