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.
Uncommon 1,2-Migration of a Nitro Group Within a β-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details / L., Bianchi; Ghelfi, Franco; G., Giorgi; M., Maccagno; G., Petrillo; D., Spinelli; M., Stenta; C., Tavani. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - 2013:28(2013), pp. 6298-6309. [10.1002/ejoc.201300856]
Uncommon 1,2-Migration of a Nitro Group Within a β-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details
GHELFI, Franco;
2013
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.
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