Synthesis of cyclic gem-dinitro compounds via radical nitration of 1,6-diynes with Fe(NO3)3·9H2O

Xiaofei Yi; Kai Chen; Wei Chen; Wanzhi Chen; Miaochang Liu; Huayue Wu

doi:10.1039/C9OB00431A

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Synthesis of cyclic gem-dinitro compounds via radical nitration of 1,6-diynes with Fe(NO₃)₃·9H₂O†

Xiaofei Yi,^a Kai Chen,^a Wei Chen,^a Wanzhi Chen,

*^a Miaochang Liu

^b and Huayue Wu

*^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, Zhejiang University, Hangzhou 310007, China
E-mail: chenwzz@zju.edu.cn

^b College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, China
E-mail: huayuewu@wzu.edu.cn

Abstract

Cyclic gem-dinitro compounds were obtained via nitration of 1,6-diynes using Fe(NO₃)₃·9H₂O as the nitrating agent. The reaction proceeds at room temperature using a cheap nitrating agent. A number of gem-dinitro cyclic compounds were obtained in moderate to good yields. The reaction offers an easy and convenient protocol to prepare gem-dinitro compounds, which are not easily obtained via the known procedures.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00431A
Article type: Communication
Submitted: 21 Feb 2019
Accepted: 23 Apr 2019
First published: 23 Apr 2019

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Org. Biomol. Chem., 2019,17, 4725-4728

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Synthesis of cyclic gem-dinitro compounds via radical nitration of 1,6-diynes with Fe(NO₃)₃·9H₂O

X. Yi, K. Chen, W. Chen, W. Chen, M. Liu and H. Wu, Org. Biomol. Chem., 2019, 17, 4725 DOI: 10.1039/C9OB00431A

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Organic & Biomolecular Chemistry