Electrophilic reactions of the dibenzo[ a , d ]tropylium ion | Zendy

Henninger Joachim | Zendy; Mayr Herbert | Zendy; Patz Matthias | Zendy; Stanescu Michaela Dina | Zendy

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Electrophilic reactions of the dibenzo[ a , d ]tropylium ion

Author(s) -

Henninger Joachim,

Mayr Herbert,

Patz Matthias,

Stanescu Michaela Dina

Publication year - 1995

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.1995199511281

Subject(s) - carbocation , chemistry , electrophile , nucleophile , hydride , ion , medicinal chemistry , computational chemistry , kinetics , photochemistry , organic chemistry , catalysis , physics , quantum mechanics , hydrogen

The kinetics of the hydride transfer reactions of the dibenzo‐tropylium ion ( 2 ) with dimethylphenylsilane ( 5 ) and triphenylsilane ( 6 ) were used to determine its electrophilicity parameter E = ‐0.71. The nucleophiles 7–9 react 10–40 times faster with 2 than expected from the linear free energy relationship (1), probably due to the formation of a ‐stabilized carbocation (e.g. 15 ). A detailed investigation of the reaction of 2 with isobutene ( 4 ) shows that the linear addition product 13a and the cyclization products are not formed via a common intermediate.

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