Synlett 2020; 31(14): 1343-1348
DOI: 10.1055/s-0040-1707145
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© Georg Thieme Verlag Stuttgart · New York

Force-Induced Cycloaddition of Aziridine: Can We Force a New Route?

Sangmin Jung
,
Seo Yeon Kim
,
Hyo Jae Yoon
This work was supported by the National Research Foundation of Korea (NRF-2019R1A6A1A11044070; NRF-2019R1A2C2011003).
Further Information

Publication History

Received: 11 May 2020

Accepted after revision: 15 May 2020

Publication Date:
18 June 2020 (online)


Abstract

Cycloaddition reactions of aziridines with dipolarophiles under traditional thermal or photochemical conditions entail destructive routes to form reactive intermediates such as an azomethine ylide. This article highlights a recent study that demonstrates a cycloaddition reaction of aziridine induced by mechanical force. Experimental results suggest that the force-induced cycloaddition of aziridine with dimethyl acetylenedicarboxylate as a dipolarophile does not seem to involve an ylide, with implications for a possible new reaction route.

1 Rivalry between Aziridine and Epoxide

2 Mechanochemically Responsive Polymers

3 Aziridine Mechanophore

4 Concluding Remarks and Outlook