The First Examples of [3+2] Cycloadditions with the Participation of (E)-3,3,3-Tribromo-1-Nitroprop-1-Ene

Karolina Zawadzińska; Zuzanna Gadocha; Kamila Pabian; Aneta Wróblewska; Ewelina Wielgus; Radomir Jasiński

doi:10.3390/ma15217584

The First Examples of [3+2] Cycloadditions with the Participation of (E)-3,3,3-Tribromo-1-Nitroprop-1-Ene

Materials (Basel). 2022 Oct 28;15(21):7584. doi: 10.3390/ma15217584.

Authors

Karolina Zawadzińska¹, Zuzanna Gadocha¹, Kamila Pabian¹, Aneta Wróblewska², Ewelina Wielgus², Radomir Jasiński¹

Affiliations

¹ Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland.
² Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.

Abstract

The first examples of [3+2] cycloaddition reactions between 3,3,3-tribromo-1-nitroprop-1-ene (TBMN) were explored on the basis of experimental and theoretical approaches. It was found that reactions involving TBMN and diarylnitrones realized with full regio- and stereoselectivity lead to respective 3,4-cis-4,5-trans-4-nitroisoxazolidines. The regioselecticity and the molecular mechanism of title processes was analyzed on the basis of the advanced DFT computational study.

Keywords: 3,3,3-tribromo-1-nitroprop-1-ene; [3+2] cycloaddition; molecular electron density theory; molecular mechanism; nitrones.

Grants and funding

This research received no external funding.