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Letters in Organic Chemistry

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

DOI: 10.2174/157017807781024165

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

Page: [268 - 272] Pages: 5

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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