Uncommon 1,2-Migration of a Nitro Group Within a β-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details
Articolo
Data di Pubblicazione:
2013
Citazione:
Uncommon 1,2-Migration of a Nitro Group Within a β-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details / L., B., Ghelfi, F., G., G., M., M., G., P., D., S., M., S., C., T.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - 2013:28(2013), pp. 6298-6309. [10.1002/ejoc.201300856]
Abstract:
The unusual migration of a nitro group from the β- to the α-
position of a β-aryl-α-nitroethenyl moiety, following a nitrocyclopropane
to isoxazoline N-oxide isomerization, has been
studied from a mechanistic and synthetic points of view. As a result, two series of isomeric isoxazoline N-oxides could
be obtained under controlled conditions. When reacted with
diazomethane, a model transposed isoxazoline cleanly furnished
a new, interesting pyrazolylisoxazole.
position of a β-aryl-α-nitroethenyl moiety, following a nitrocyclopropane
to isoxazoline N-oxide isomerization, has been
studied from a mechanistic and synthetic points of view. As a result, two series of isomeric isoxazoline N-oxides could
be obtained under controlled conditions. When reacted with
diazomethane, a model transposed isoxazoline cleanly furnished
a new, interesting pyrazolylisoxazole.
Tipologia CRIS:
Articolo su rivista
Keywords:
Synthetic methods / Heterocycles / Nitro group migration / Alkenes
Elenco autori:
L., Bianchi; Ghelfi, Franco; G., Giorgi; M., Maccagno; G., Petrillo; D., Spinelli; M., Stenta; C., Tavani
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