2022
DOI: 10.1248/cpb.c21-00673
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of <i>N</i>-Aminated Salts of Aliphatic <i>tert</i>-Amines, (Trialkyl)amidines, and (Pentaalkyl)guanidines by Electrophilic Amination in an Ethereal Solvent

Abstract: The electrophilic amination of nitrogen-based nucleophiles, including strong organic bases, was conducted in an Et 2 O solvent using O-(mesitylenesulfonyl)hydroxylamine. Aliphatic tert-amines and N,N,N′-(trialkyl) amidines rapidly formed precipitates of the corresponding aminated salts in high yields. The amination of the highly basic and sterically hindered N,N,N′,N′,N″-(pentaalkyl)guanidines was achieved under modified conditions, although the yields were moderate because of a competing side reaction caused … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
1
0

Year Published

2024
2024
2024
2024

Publication Types

Select...
1

Relationship

0
1

Authors

Journals

citations
Cited by 1 publication
(1 citation statement)
references
References 32 publications
0
1
0
Order By: Relevance
“…Salts 4a-d were readily prepared by electrophilic N-amination of Me3N, Et3N, quinuclidine, and 1-azanorbornane using O-(mesitylenesulfonyl) hydroxylamine in Et2O, as we previously reported. 24 Because heat-induced decomposition has been reported for Gornostaev's ylide 2, the thermal stability of 5a-d was briefly examined by heating their odichlorobenzene solution to 140 °C (Figure 2B). Me3N + N − --nitrobenzene 5a decomposed moderately in 4 h, leaving 59% of its initial quantity.…”
mentioning
confidence: 99%
“…Salts 4a-d were readily prepared by electrophilic N-amination of Me3N, Et3N, quinuclidine, and 1-azanorbornane using O-(mesitylenesulfonyl) hydroxylamine in Et2O, as we previously reported. 24 Because heat-induced decomposition has been reported for Gornostaev's ylide 2, the thermal stability of 5a-d was briefly examined by heating their odichlorobenzene solution to 140 °C (Figure 2B). Me3N + N − --nitrobenzene 5a decomposed moderately in 4 h, leaving 59% of its initial quantity.…”
mentioning
confidence: 99%