Electrophilic reactions of the dibenzo[a,d]tropylium ion
โ 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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โฆ Synopsis
Abstract
The kinetics of the hydride transfer reactions of the dibenzoโtropylium ion (2) with dimethylphenylsilane (5) and triphenylsilane (6) were used to determine its electrophilicity parameter E = โ0.71. The nucleophiles 7โ9 react 10โ40 times faster with 2 than expected from the linear free energy relationship (1), probably due to the formation of a โstabilized 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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