Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene

Kento Iwai; Khimiya Wada; Nagatoshi Nishiwaki

doi:10.3390/molecules27154804

Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene

Molecules. 2022 Jul 27;27(15):4804. doi: 10.3390/molecules27154804.

Authors

Kento Iwai^{1

2}, Khimiya Wada¹, Nagatoshi Nishiwaki^{1

2}

Affiliations

¹ School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.
² Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.

Abstract

Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyrene with an amine; however, subsequent C-C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the trans-isomer to a cis-isomer did not occur efficiently, even when UV light was irradiated. We studied these unusual behaviors of β-nitrostyrene, focusing on the role of the ortho-hydroxy group.

Keywords: 1,3-dipolar cycloaddition; C–C bond cleavage; conjugate addition; nitrostyrene; photoisomerization.

MeSH terms

Isomerism
Styrenes* / chemistry

Substances

Styrenes
beta-nitrostyrene

Grants and funding

This research received no external funding.