The stepwise oxidation of indolino[2,1-b]oxazolidine derivatives

Rachid Hadji (1) , György Szalóki (1) , Olivier Alévêque (1) , Eric Levillain (1) , Lionel Sanguinet (1)

1 MOLTECH-Anjou

This work presents an original strategy to modulate the electrochemical properties of the indolino[2,1-b]oxazolidine core appropriately substituted in position 5 (para-substitution of the phenyl ring) by acceptor or donor groups (CHO, OMe, Me, F, H, Cl, Br). Supported by spectroelectrochemical experiments and confronted to electrochemical simulations, the stepwise oxidation of indolino[2,1-b]oxazolidine derivatives involves an electrochemical mechanism which depends on the para-substitution of the phenyl ring and leads to either the formation of a stable radical cation, the opening of the oxazolidine ring or an irreversible aryl C–C coupling.

Mots clés: indolino[2 1-b]oxazolidine; Cyclic voltammetry; Electrochemical simulations; Multi-responsive systems; Spectroelectrochemistry

Domaines: Autre

Rachid Hadji, György Szalóki, Olivier Alévêque, Eric Levillain, Lionel Sanguinet. The stepwise oxidation of indolino[2,1-b]oxazolidine derivatives. Journal of Electroanalytical Chemistry, 2015, 749, pp.1-9. ⟨10.1016/j.jelechem.2015.04.032⟩. ⟨hal-01390948⟩