School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.
Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.
Molecules. 2022 Jul 27;27(15):4804. doi: 10.3390/molecules27154804.
Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, -hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the -hydroxy-β-nitrostyrene with an amine; however, subsequent C-C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the -isomer to a -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 -hydroxy group.
硝酮类衍生物在有机合成中被广泛用作迈克尔加成、光异构化和环加成的底物。相比之下，-羟基衍生物在这些反应中表现出异常的行为。β-羟基-β-硝基苯乙烯与胺反应时发生共轭加成；然而，随后的 C-C 键容易断裂，生成相应的亚胺。此外，即使受到紫外光照射，-异构体也不易转化为-异构体。我们研究了β-硝基苯乙烯的这些异常行为，重点关注-羟基的作用。
