trans-1,2-Disiloxybenzocyclobutene + O 2 & pseudopotentials for hybridized carbon atoms

Yannick Carissan (1)

1 CTOM - Chimie Theorique et Modèles

The trans-1,2-Disiloxybenzocyclobutene (1) exists as a yellow liquid at room temperature. It exhibits a thermochromic behavior (it is colorless at 3°C) and a combined experimental and theoretical study showed that it traps 3O2.[1] This later reaction is considered to be forbidden because (1) has a singlet ground state. In this contribution, we shall give an explanation to the thermocromicity and suggest a reaction path between (1) and 3O2, which matches experimental facts. Finally, we will suggest modifications to be done on (1) to tune its properties.[2] REFERENCES [1] Drujon, J., Rahmani, R.,Héran, V., Blanc, R., Carissan, Y., Tuccio, B., Commeiras, L., Parrain, J.-L., “trans-1,2-Disiloxybenzocyclobutene, an adequate partner for the auto-oxidation: EPR/spin trapping and theoretical studies”, Phys. Chem. Chem. Phys., 16, 7513-7520 (2014) [2] Nava, P., Carissan, Y., “On the ring-opening of substituted cyclobutene to benzocyclobutene: analysis of π delocalization, hyperconjugation, and ring strain”, Phys. Chem. Chem. Phys., 16, 16196-16203 (2014)

Domains: Chemical Sciences; Theoretical and/or physical chemistry

Yannick Carissan. trans-1,2-Disiloxybenzocyclobutene + O 2 & pseudopotentials for hybridized carbon atoms. Joint EMLG/JMLG Annual Meeting, Janis Samios, Sep 2016, Platanias, Greece. ⟨hal-01408042⟩