Display options
Cite
Miao M, Luo Y, Xu H, et al. Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles. J Org Chem. 2017;82(23):12224-12237doi: 10.1021/acs.joc.7b02087.
Miao, M., Luo, Y., Xu, H., Jin, M., Chen, Z., Xu, J., & Ren, H. (2017). Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles. The Journal of organic chemistry, 82(23), 12224-12237. https://doi.org/10.1021/acs.joc.7b02087
Miao, Maozhong, et al. "Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles." The Journal of organic chemistry vol. 82,23 (2017): 12224-12237. doi: https://doi.org/10.1021/acs.joc.7b02087
Miao M, Luo Y, Xu H, Jin M, Chen Z, Xu J, Ren H. Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles. J Org Chem. 2017 Dec 01;82(23):12224-12237. doi: 10.1021/acs.joc.7b02087. Epub 2017 Oct 30. PMID: 29058419.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2017 Dec 01;82(23):12224-12237. doi: 10.1021/acs.joc.7b02087. Epub 2017 Oct 30.

Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles.

The Journal of organic chemistry

Maozhong Miao, Yi Luo, Huaping Xu, Mengchao Jin, Zhengkai Chen, Jianfeng Xu, Hongjun Ren

Affiliations

  1. Department of Chemistry, Zhejiang Sci-Tech University , Hangzhou, Zhejiang 310018, P. R. China.

PMID: 29058419 DOI: 10.1021/acs.joc.7b02087

Abstract

The tunable nucleophilic nitration of 3-cyclopropylideneprop-2-en-1-ones with cheap sodium nitrite is described. This transformation proceeds with the assistance of a strained cyclopropane ring and allows for a divergent route to various synthetically useful β,γ-dinitro or γ-mononitro adducts in high yields with exclusive regio- and stereoselectivity. Additionally, a wide array of valuable functionalized N-unprotected pyrroles is achieved from the resulting β,γ-dinitro compounds via reductive cyclization strategy.

Publication Types