|
Hydroxamic acids can also be synthesized from [[aldehyde]]s and ''N''-sulfonylhydroxylamine via the [[Angeli-Rimini reaction]].[{{cite book |last1=Li |first1=Jie Jack |title=Name Reactions: A Collection of Detailed Reaction Mechanisms |date=2003 |publisher=Springer |location=Berlin, Heidelberg, New York |isbn=978-3-662-05338-6 |page=9 |edition=2nd}}] Alternatively, [[molybdenum oxide diperoxide]] oxidizes [[trimethylsilyl|trimethylsilated]] [[amide]]s to hydroxamic acids, although yields are only about 50%.[{{cite journal|year=1979|pages=2481–2487|title=The oxidation of trimethylsilylated amides to hydroxamic acids|first1=Stephen A.|last1=Matlin|first2=Peter G.|last2=Sammes|first3=Roger M.|last3=Upton|journal=Journal of the Chemical Society, Perkin Transactions 1|doi=10.1039/p19790002481 }}] |
|
Hydroxamic acids can also be synthesized from [[aldehyde]]s and ''N''-sulfonylhydroxylamine via the [[Angeli-Rimini reaction]].[{{cite book |last1=Li |first1=Jie Jack |title=Name Reactions: A Collection of Detailed Reaction Mechanisms |date=2003 |publisher=Springer |location=Berlin, Heidelberg, New York |isbn=978-3-662-05338-6 |page=9 |edition=2nd}}] Alternatively, [[molybdenum oxide diperoxide]] oxidizes [[trimethylsilyl|trimethylsilated]] [[amide]]s to hydroxamic acids, although yields are only about 50%.[{{cite journal|year=1979|pages=2481–2487|title=The oxidation of trimethylsilylated amides to hydroxamic acids|first1=Stephen A.|last1=Matlin|first2=Peter G.|last2=Sammes|first3=Roger M.|last3=Upton|journal=Journal of the Chemical Society, Perkin Transactions 1|doi=10.1039/p19790002481 }}] |
|
In a variation on the [[Nef reaction]], [[Primary carbon|primary]] [[nitro compounds]] kept in an acidic solution (to minimize the [[nitronate]] [[tautomer]]) hydrolyze to a hydroxamic acid.[Smith (2020), ''March's Organic Chemistry'', rxn. 16-3.] Said reaction may also require photoexcitation to the [[triplet state]]; for secondary nitro compounds, the photoreaction proceeds with a [[Beckmann rearrangement|Beckmann-like]] ring expansion.[{{Cite journal|doi=10.1021/cr00004a002|pp=478–479|journal=Chemical Reviews|year=1991|volume=91|title=Photochemistry of hydroxamic acids and derivatives|first=Ewa|last=Lipzcynska-Kochany|orig-date=March 22, 1991}}] |
|
In a variation on the [[Nef reaction]], [[Primary carbon|primary]] [[nitro compounds]] kept in an acidic solution (to minimize the [[nitronate]] [[tautomer]]) hydrolyze to a hydroxamic acid.[Smith (2020), ''March's Organic Chemistry'', rxn. 16-3.] In base, the reaction requires photoexcitation to the [[triplet state]], and for secondary nitro compounds, the photoreaction proceeds with a [[Beckmann rearrangement|Beckmann-like]] ring expansion.[{{Cite journal|doi=10.1021/cr00004a002|pp=478–479|journal=Chemical Reviews|year=1991|volume=91|title=Photochemistry of hydroxamic acids and derivatives|first=Ewa|last=Lipzcynska-Kochany|orig-date=March 22, 1991}}] |
|
A well-known reaction of hydroxamic acid esters is the [[Lossen rearrangement]].[{{cite book |last1=Wang |first1=Zerong |title=Comprehensive organic name reactions and reagents |date=2010 |publisher=John Wiley & Sons, Inc. |isbn=9780471704508 |pages=1772–1776}}] |
|
A well-known reaction of hydroxamic acid esters is the [[Lossen rearrangement]].[{{cite book |last1=Wang |first1=Zerong |title=Comprehensive organic name reactions and reagents |date=2010 |publisher=John Wiley & Sons, Inc. |isbn=9780471704508 |pages=1772–1776}}] |
Like
0
Dislike
0
Love
0
Funny
0
Angry
0
Sad
0
Wow
0
