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

Lara Bianchi; Gianluca Giorgi; Massimo Maccagno; Giovanni Petrillo; Egon Rizzato; Domenico Spinelli; Marco Stenta; Cinzia Tavani

doi:10.2174/157017807781024165

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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Letters in Organic Chemistry

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

Volume: 4 Issue: 4

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

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

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.

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Lara Bianchi , Gianluca Giorgi , Massimo Maccagno , Giovanni Petrillo , Egon Rizzato , Domenico Spinelli , Marco Stenta and Cinzia Tavani , An Unprecedented “Reverse” 1,2-Migration of a Nitro Group within an α-Aryl-β-nitroethenyl Moiety Driven by Steric and Stereoelectronic Effects, Letters in Organic Chemistry 2007; 4 (4) . https://dx.doi.org/10.2174/157017807781024165