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

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.

Automated summary

In this study, the first examples of [3+2] cycloaddition reactions between 3,3,3-tribromo-1-nitroprop-1-ene and diarylnitrones were explored, leading to the formation of 3,4-cis-4,5-trans-4-nitroisoxazolidines with full regio- and stereoselectivity. The regioselectivity and molecular mechanism of these processes were analyzed using advanced DFT computational study.