Journal
TETRAHEDRON
Volume 67, Issue 25, Pages 4664-4671Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.04.065
Keywords
Dendrimer; Carbocation; Electrochemical oxidation; Friedel-Crafts alkylation
Categories
Funding
- MEXT [2105]
- Asahi Glass Foundation
- JST
- Grants-in-Aid for Scientific Research [21106001, 23750127, 21106002] Funding Source: KAKEN
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Dendritic diarylcarbenium ion pools were synthesized by the low temperature electrochemical oxidation of the corresponding dendritic (diarylmethyl)trimethylsilanes, which were prepared by use of the iterative method consisting of electrochemical activation and Friedel Crafts type coupling. Time-course NMR studies revealed that thermal stability of dendritic diarylcarbenium ions depends both on the generation of the dendritic structure and on the para-substituents of the terminal phenyl groups. Dendritic diarylcarbenium ions up to the third generation exhibited high reactivity as a carbon electrophile. (C) 2011 Elsevier Ltd. All rights reserved.
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