Substituent effects in Scholl-type reactions of 1,2-terphenyls to triphenylenes
A series of 3,3’’- and 4,4’’-dimethoxy terphenyls with different second substituents on their ortho-positions have been synthesized and investigated upon the possibility to be oxidatively cyclodehydrogenated to the corresponding triphenylenes under Scholl-type conditions. The experimentally obtained...
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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
December 13, 2024
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| In: |
Chemistry - a European journal
Year: 2024, Volume: 30, Issue: 70, Pages: 1-9 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202402821 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202402821 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202402821 
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| Author Notes: | Dennis Reinhard, Moritz P. Schuldt, Sven M. Elbert, Lucas Ueberricke, Karsten Hengefeld, Frank Rominger, and Michael Mastalerz |
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| 245 | 1 | 0 | |a Substituent effects in Scholl-type reactions of 1,2-terphenyls to triphenylenes |c Dennis Reinhard, Moritz P. Schuldt, Sven M. Elbert, Lucas Ueberricke, Karsten Hengefeld, Frank Rominger, and Michael Mastalerz |
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| 520 | |a A series of 3,3’’- and 4,4’’-dimethoxy terphenyls with different second substituents on their ortho-positions have been synthesized and investigated upon the possibility to be oxidatively cyclodehydrogenated to the corresponding triphenylenes under Scholl-type conditions. The experimentally obtained selectivities were supported and explained by quantum chemical calculations and conclusions on the involved mechanisms (acid catalyzed arenium-ion mechanism (AIM) vs radical cation mechanism) were drawn. | ||
| 650 | 4 | |a Arenium ion | |
| 650 | 4 | |a Cyclodehydrogenative coupling | |
| 650 | 4 | |a Radical cation | |
| 650 | 4 | |a Scholl reaction | |
| 650 | 4 | |a Selectivity | |
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