Synthesis of 3-(5-nitrocyclohex-1-enyl) acrylic acid and...

C - Chemistry – Metallurgy – 07 – C

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C07C 201/06 (2006.01) C07C 205/55 (2006.01) C07C 251/44 (2006.01)

Patent

CA 2656241

This application discloses provides a process for the introduction of nitro-group functionality into a compound which contains also a site of unsaturation and/or oxygen functionality by direct (one step) oxidation of an oxime functional group mediated by a molybdenum VI/VII peroxo complex, the process comprising: (a) providing a substrate of Formula I containing an oxime functional group; Chemical formula should be inserted here as it appears on the abstract in paper form. wherein R1 and R2 are selected independently from linear, branched or cyclic alkyl and linear, branched or cyclic alkenyl groups, optionally substituted, with the proviso that at least one of R1 or R2 contains a carbon/carbon double bond; and (b) contacting said substrate of Formula I with a molybdenum oxidation complex, thereby oxidizing said oxime functional group to a nitro functional group to yield the structure of Formula III. Chemical formula should be inserted here as it appears on the abstract in paper form. Where R1 and R2 are as defined above.

L'invention concerne un procédé pour introduire une fonction nitro dans un composé comportant également un site d'insaturation et/ou une fonction oxygène, par oxydation directe (en une étape) d'un groupe fonctionnel oxime dont la médiation est assurée par un complexe molybdène VI/VII peroxo. Le procédé selon l'invention comprend les étapes qui consistent : (a) à fournir un substrat de formule (I) qui contient un groupe fonctionnel oxime, R1 et R2 étant sélectionnés indépendamment parmi des groupes alkyle linéaires, ramifiés ou cycliques et des groupes alcényle linéaires, ramifiés ou cycliques, éventuellement substitués, à condition que R1 ou R2 comporte une double liaison carbone/carbone; et (b) à mettre en contact le substrat de formule (I) avec un complexe d'oxydation molybdène, pour induire l'oxydation du groupe fonctionnel oxime en groupe fonctionnel nitro et ainsi obtenir une structure de formule (III).

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