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Reactivity vs. Stability of Cyclopropenium Substituted Phosphonium Salts
Author(s) -
Taakili Rachid,
Duhayon Carine,
Lugan Noël,
Canac Yves
Publication year - 2019
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201900867
Subject(s) - reactivity (psychology) , steric effects , phosphonium , nucleophile , chemistry , allene , electrophile , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.