Cyclization of terphenyl-bisfluorenol a mechanistic study of the regioselectvity

Cyril Poriel (1) , F Barriere (1) , Joëlle Rault-Berthelot (1) , Damien Thirion (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

The mechanism of the bicyclization reaction of a series of terphenyl-bisfluorenols into dispiro[fluorene-9,6'-indeno[1,2-b]fluorene-12',9''-fluorene] and dispiro[fluorene-9,6'-indeno[2,1-a]fluorene-12',9''-fluorene] is reported. Through a combined experimental and theoretical study, the different parameters that drive the regioselectivity of this cyclization reaction have been studied and are presented.

Keywords: mechanistic investigations; regioselectivity; spiro compounds; pi-conjugated systems; cyclization

Domains: Chemical Sciences; Organic chemistry

Cyril Poriel, F Barriere, Joëlle Rault-Berthelot, Damien Thirion. Cyclization of terphenyl-bisfluorenol a mechanistic study of the regioselectvity. Chemistry - A European Journal, 2019, 25 (45), pp.10689-10697. ⟨10.1002/chem.201901457⟩. ⟨hal-02150454⟩