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endo-Selectivity in the cycloaddition reactions of tropylium ion

✍ Scribed by Shô Itô; Isamu Itoh; Ikuo Saito; Akira Mori

Book ID
104243157
Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
138 KB
Volume
15
Category
Article
ISSN
0040-4039

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New Diels-Alder reactions of tropylium ion are studied, and the observed stereoselectivities suggest that solvent effects determine the steric course of these reactions. Troplylium ion (1) has been found to undergo a number of Diels-Alder type reactions with high endo selectivity.2

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## Abstract 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 f