Reaction of antiaromatic porphyrinoid with active methylene compounds

Demin Ren; Xinliang Fu; Xiaofang Li; Sebastian Koniarz; Piotr J. Chmielewski

doi:10.1039/C9QO00679F

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Reaction of antiaromatic porphyrinoid with active methylene compounds†

Demin Ren,^a Xinliang Fu,^a Xiaofang Li,

*^a Sebastian Koniarz

^b and Piotr J. Chmielewski

*^b

Author affiliations

* Corresponding authors

^a Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology Xiangtan, Hunan 411201, China
E-mail: lixiaofang@iccas.ac.cn

^b Department of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50 383 Wrocław, Poland
E-mail: piotr.chmielewski@chem.uni.wroc.pl

Abstract

Active methylene compounds which have two electron-withdrawing groups, such as ethyl 2-cyanoacetate, 3-oxobutanenitrile, cyclohexane-1,3-dione, malononitrile, pentane-2,4-dione, and ethyl acetoacetate, react regioselectively with antiaromatic norcorrolatonickel(II) in THF at room temperature in the presence of Cs₂CO₃ yielding new types of norcorrole derivatives retaining the spectral, magnetic, and redox properties of the starting macrocycle.

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DOI: https://doi.org/10.1039/C9QO00679F
Article type: Research Article
Submitted: 23 May 2019
Accepted: 27 Jun 2019
First published: 28 Jun 2019

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Org. Chem. Front., 2019,6, 2924-2933

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Reaction of antiaromatic porphyrinoid with active methylene compounds

D. Ren, X. Fu, X. Li, S. Koniarz and P. J. Chmielewski, Org. Chem. Front., 2019, 6, 2924 DOI: 10.1039/C9QO00679F

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Reaction of antiaromatic porphyrinoid with active methylene compounds†

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Reaction of antiaromatic porphyrinoid with active methylene compounds

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