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 Nitrogroup within a β Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details
BIANCHI, LARA;MACCAGNO, MASSIMO;PETRILLO, GIOVANNI;TAVANI, CINZIA
2013-01-01
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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