Reactivity vs. Stability of Cyclopropenium Substituted Phosphonium Salts

Rachid Taakili (1) , Carine Guyard-Duhayon (1) , Noël Lugan (1) , Yves Canac (1)

1 LCC - Laboratoire de chimie de coordination

The stability vs. reactivity of electrophilic 3-(triphenylphosphonio)-cyclopropenium salts towards a neutral nucleophile, such as triphenylphosphane, is reported. Depending on the nature of cyclopropenyl substituents (R), the three-membered cyclic structure is preserved (R = Ph) or evolves by ring opening to the isomeric linear allene (R = Mes). The respective formation of 1,3-bis(triphenylphosphonio)-2,3-diphenylcyclopropene and 3,3-bis(triphenylphosphonio)-1,1-dimesitylallene products is rationalized on the basis of steric and electrostatic constraints.

Mots clés: Allene; charge; cyclopropene; cyclopropenium; phosphonium; ring strain 2

Domaines: Chimie de coordination

Rachid Taakili, Carine Guyard-Duhayon, Noël Lugan, Yves Canac. Reactivity vs. Stability of Cyclopropenium Substituted Phosphonium Salts. European Journal of Inorganic Chemistry, 2019, 2019 (36), pp.3982-3989. ⟨10.1002/ejic.201900867⟩. ⟨hal-02335192⟩