Nucleophilic Reactivities of Ketene Acetals | Zendy

Tokuyasu Takahiro | Zendy; Mayr Herbert | Zendy

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Nucleophilic Reactivities of Ketene Acetals

Author(s) -

Tokuyasu Takahiro,

Mayr Herbert

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400134

Subject(s) - ketene , chemistry , electrophile , nucleophile , reactivity (psychology) , reaction rate constant , computational chemistry , kinetics , ion , medicinal chemistry , photochemistry , organic chemistry , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics

The kinetics of the reactions of ketene acetals with benzhydrylium ions have been followed photometrically. The reactions proceed with rate‐determining C−C bond formation that is considerably faster than expected for outer‐sphere electron transfer processes. Structure−reactivity relationships are discussed. The excellent correlations between the observed second‐order rate constants (log k 2 ) and the previously reported electrophilicity parameters ( E ) of benzhydrylium ions suggest that several of the compounds investigated in this work can be used as reference nucleophiles for the development of electrophilicity scales. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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