3 years ago

Synthesis of Ferrocenyl-Based Unsymmetrical Azines via a Simple Reaction of Aldehydes with Ketone-Derived N-Tosyl Hydrazones and the Evaluation of the Extent of Conjugation in the Molecule

Synthesis of Ferrocenyl-Based Unsymmetrical Azines via a Simple Reaction of Aldehydes with Ketone-Derived N-Tosyl Hydrazones and the Evaluation of the Extent of Conjugation in the Molecule
Jianfeng Hu, Junyang Dong, Hao Zhang, Jianhua Cheng, Yi Luo, Qiang Teng, Yufeng Liu
We have designed and synthesized 1-substituted and 1,1′-disubstituted ferrocene-based unsymmetrical azines under metal-free conditions. The crystal structures of 3k, 5i, and 5g revealed that conjugative interactions between the ferrocene phenyl rings and the entire azine fragment exist. Furthermore, our electrochemical and optical analysis provided support for extended conjugation, which suggested a larger substituent effect in this system. Density functional theory calculations also supported the results. Thus, these results reflect a stronger conjugative interaction between the ferrocene phenyl rings and the entire azine fragment.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00366

DOI: 10.1021/acs.organomet.7b00366

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