Substituent Effects in Scholl-Type Reactions of 1,2-Terphenyls to Triphenylenes.

Autor: Reinhard D; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany., Schuldt MP; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany., Elbert SM; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany., Ueberricke L; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany., Hengefeld K; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany., Rominger F; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany., Mastalerz M; Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 272, 69120, Heidelberg, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Dec 13; Vol. 30 (70), pp. e202402821. Date of Electronic Publication: 2024 Nov 03.
DOI: 10.1002/chem.202402821
Abstrakt: 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.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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