An Unprecedented “Reverse” 1,2-Migration of a Nitro Group within an α-Aryl-β-nitroethenyl Moiety Driven by Steric and Stereoelectronic Effects

Author(s): Lara Bianchi, Gianluca Giorgi, Massimo Maccagno, Giovanni Petrillo, Egon Rizzato, Domenico Spinelli, Marco Stenta, Cinzia Tavani.

Journal Name: Letters in Organic Chemistry

Volume 4 , Issue 4 , 2007

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Abstract:

The release of repulsive interactions of steric and/or stereoelectronic nature and the onset of a new extended and effective conjugation concur to an unprecedented and synthetically appealing shift of a nitro group from the β- to the α-position with respect to the aryl group of a styrene moiety.

Keywords: Nitro group migration, isoxazoline N-oxides, nitroalkenes, DFT calculations, vinylcyclopropanes

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Article Details

VOLUME: 4
ISSUE: 4
Year: 2007
Page: [268 - 272]
Pages: 5
DOI: 10.2174/157017807781024165
Price: $65

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