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Unravelling the mechanism of force-induced ring-opening of benzocyclobutenes

Ribas-Arino, J.*; Shiga, Motoyuki   ; Marx, D.*

By exploring force-transformed potential energy surfaces of both $$cis$$ and $$trans$$ 1,2-disubstitutedbenzocyclobutene molecule, we unravel the mechanism of force-induced ring-opening. The expected conrotatory process of $$cis$$ reactant leading to $$E$$,$$Z$$ product is only observed at very small forces, whereas disrotatory ring-opening yields $$E$$,$$E$$ diene at larger forces, which is shown to be a concerted process.

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Category:Chemistry, Multidisciplinary

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