2001
DOI: 10.1016/s0040-4039(01)01745-2
|View full text |Cite
|
Sign up to set email alerts
|

A convenient synthesis of secondary hydroxylamines

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
24
0
1

Year Published

2004
2004
2010
2010

Publication Types

Select...
5
1
1

Relationship

0
7

Authors

Journals

citations
Cited by 39 publications
(25 citation statements)
references
References 30 publications
0
24
0
1
Order By: Relevance
“…52 Finally, another useful way to convert secondary amines into the corresponding hydroxylamines involves sequential Michael addition to acrylonitrile, oxidation to the N-oxide level using mCPBA and lastly a Cope elimination of acrylonitrile. 55 …”
Section: Alternative Strategies For Hydroxylamine Formationmentioning
confidence: 99%
“…52 Finally, another useful way to convert secondary amines into the corresponding hydroxylamines involves sequential Michael addition to acrylonitrile, oxidation to the N-oxide level using mCPBA and lastly a Cope elimination of acrylonitrile. 55 …”
Section: Alternative Strategies For Hydroxylamine Formationmentioning
confidence: 99%
“…The cyanoethyl group undergoes facile Cope elimination from initially formed N-oxide (e.g. 137, equation 91) thus giving the corresponding hydroxylamine 138 in a good yield 276,277 . 278 .…”
Section: Hydroxylamines Through Oxidation Of Aminesmentioning
confidence: 99%
“…Trialkylamine oxides may be pyrolyzed to yield an alkene plus an N,N-dialkylhydroxylamine (Cope elimination). [332][333][334][335][336][337][338][339][340][341][342][343] It should be emphasized that this method is only useful for the synthesis of N-(lower alkyl)-N-methylhydroxylamines and N,N-dialkylhydroxylamines with identical alkyl residues, e.g. 255, because otherwise mixtures of hydroxylamines are obtained.…”
mentioning
confidence: 99%
“…[335] Oxidation of a range of 2-cyanoethyl tertiary amines 257 with 3-chloroperoxybenzoic acid in dichloromethane, followed by Cope elimination of the transient intermediate Noxides 258, gives several (cyclic) N,N-dialkylhydroxylamines 259 in excellent yields (Scheme 95). [342] Scheme 95 Synthesis of (Cyclic) N,N-Dialkylhydroxylamines from 2-Cyanoethyl Tertiary Amines [342] N ( )…”
mentioning
confidence: 99%
See 1 more Smart Citation