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

โœ Scribed by Henninger, Joachim ;Mayr, Herbert ;Patz, Matthias ;Stanescu, Michaela Dina


Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
456 KB
Volume
1995
Category
Article
ISSN
0947-3440

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โœฆ Synopsis


Abstract

The kinetics of the hydride transfer reactions of the dibenzoโ€tropylium ion (2) with dimethylphenylsilane (5) and triphenylsilane (6) were used to determine its electrophilicity parameter E = โ€0.71. The nucleophiles 7โ€“9 react 10โ€“40 times faster with 2 than expected from the linear free energy relationship (1), probably due to the formation of a โ€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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