Details

Autor(en) / Beteiligte

• Taakili, Rachid
• Duhayon, Carine
• Lugan, Noël
• Canac, Yves

Titel

Reactivity vs. Stability of Cyclopropenium Substituted Phosphonium Salts

Ist Teil von

• European journal of inorganic chemistry, 2019-09, Vol.2019 (36), p.3982-3989

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Wiley Online Library Journals Frontfile Complete

Beschreibungen/Notizen

• 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. The reactivity of cyclopropenium substituted phosphonium salts towards PPh3 is controlled by the nature of cyclopropenyl substituents, favoring either the cyclopropenic form (R = Ph) or the linear allenic form (R = Mes).