jo0489824_si_001.pdf (31.35 kB)
NaNO2-Mediated Transformation of Aliphatic Secondary Nitroalkanes into Ketones or Oximes under Neutral, Aqueous Conditions: How the Nitro Derivative Catalyzes Its Own Transformation
journal contribution
posted on 2004-12-24, 00:00 authored by Arnaud Gissot, Silvere N'Gouela, Christophe Matt, Charles MioskowskiThe nitrosation of secondary nitro derivatives into ketones or oximes depending on the nitro
substituents has been reinvestigated. The reaction efficiently takes place under neutral conditions,
thus allowing acid-sensitive substrates to be converted in very good yields. The generation of
nitrosating species under such mild conditions is unprecedented. Mechanistic investigations strongly
suggest that they result from the nucleophilic attack of the nitrite anion on the aci-nitro(nate)
form of the secondary nitroalkane. The latter acts in turn as an autocatalyst for its own
transformation by means of the nitrosating species generated in situ from it.
History
Usage metrics
Categories
Keywords
Own Transformationgenerationnitroalkanenitro substituentsoximeMediated TransformationAqueounitro derivativesnucleophilic attackNitrolatter actsketoneautocatalystNeutralCatalyzetransformationNaNO 2Ketonenitrite anionnitrosating speciesreinvestigatedsubstrateMechanistic investigationsaciNitroalkanenitrosationyieldAliphaticOxime
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC