Alcoholysis of N-acetoxy-N-alkoxycarbamates. Synthesis of NH-N,N-dialkoxyamines from N,N-dialkoxycarbamates

The alcoholysis of N-acetoxy-N-alkoxycarbamates by methanol or ethanol at 20 – 40 °C yields N,N-dialkoxycarbamates and acetic acid. At the lower temperature the competitive formation of N,N’-bis(alkoxycarbonyl)-N,N’-bis(alkoxy)hydrazines can occur. The alkaline hydrolysis of N,N-dialkoxycarbamates yields NH-N,N-dialkoxyamines

N,N-Dimethoxy-N-tert-alkylamines: new synthesis methods and the crystal structure of the precursor

Under the methanolysis of N-methoxy-N-(1-pyridinium)amines salts 1a–c, nucleophilic substitution occurs at the nitrogen atom to form N,N-dimethoxyamines 2a,b; the crystal structure of precursor 1c has been studied

New approach to N,N-dialkoxy-N'-arylureas and N,N-dialkoxycarbamates

Methanolysis of N-chloro-N-alkoxy-N'-arylureas in the presence of silver trifluoroacetate gives the corresponding N,N-dialkoxy-N'‑arylureas, whereas N-chloro-N-alkoxycarbamates react with alcohols in the presence of silver trifluoroacetate to afford N,N-dialkoxycarbamates

Methanolysis of N-acetoxy-N-n-propyloxy-N’,N’-dimethylurea in different conditions

The methanolysis of N-acetoxy-N-n-propyloxy-N’,N’-dimethylurea in the presence of strong acids at room temperatures or in the boiling methanol yields N,N-dimethoxy-N’,N’-dimethylurea as final product. Primarily the nucleophilic substitution acetoxy group at nitrogen on methoxy group arises. At second stage the transesterification of N,N-dialkoxyamino group of formed N-methoxy-N-n-propyloxy-N’,N’-dimethylurea take place

Pyramidal amide nitrogen in N-acyloxy-N-alkoxyureas and N-acyloxy-N-alkoxycarbamates

The XRD studies of N-acyloxy-N-alkoxyamides 1, 2 have revealed a highly pyramidal configuration of amide nitrogen in the O–N–O group

N,N-Dimethoxy-N-tert-alkylamines: new synthesis methods and the crystal structure of the precursor

Under the methanolysis of N-methoxy-N-(1-pyridinium)amines salts 1a–c, nucleophilic substitution occurs at the nitrogen atom to form N,N-dimethoxyamines 2a,b; the crystal structure of precursor 1c has been studied

Synthesis and structure of N-alkoxyhydrazines and N-alkoxy-N',N',N'-trialkylhydrazinium salts

New types of 1,1,1-trialkyl-2-alkoxyhydrazinium chlorides and N-alkoxyhydrazines were obtained by reactions of N-chloro-N-alkoxyureas with trimethylamine or 1,4-diaza[2.2.2]bicyclooctane and by reactions of methyl N chloro-N-methoxycarbamate with potassium salt of N-acetylbenzenesulfonylamide. The XRD studies of N,N' bis(methoxycarbonyl)-N,N'-dimethoxyhydrazine, N'-methoxy-N'‑methoxycarbonyl-N-acetylbenzenesulfonylhydrazide and 1,1,1-trimethyl-2-methoxyhydrazinium perchlorate revealed the pyramidal configuration of the central nitrogen atoms in O–N–N geminal system, unusual elongation of N–N+ bond and shortening of N–OMe bond in 1,1,1-trimethyl-2-methoxyhydrazinium perchlorate