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Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene.

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.

SUBMITTER: Iwai K

PROVIDER: S-EPMC9369901 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene.

Iwai Kento K Wada Khimiya K Nishiwaki Nagatoshi N

Molecules (Basel, Switzerland) 20220727 15

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 ...[more]

PMID: 35956754

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