Related Experiment Video
Updated: Jan 15, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Bidirectional Synthesis of C2-Symmetric Unilateral Substituted Acenes: 1,10,11,12-Tetrafluorotetracene
Ruth Esther Pessi Kenmogne1, Xiulan Xie1, Ulrich Koert1
1Department of Chemistry, Philipps University of Marburg, Hans-Meerwein-Straße 4, D-35043 Marburg, Germany.
Abstract:
The efficacy of a bidirectional synthesis for C2-symmetric acenes was demonstrated for 1,10,11,12 tetrafluorotetracene. Starting from a central naphthalene, 2-fold Suzuki cross-coupling reactions attached lower side chains to the left and right sides simultaneously. Two fluorine substitutents were introduced via MOM-directed lithiation. The Suzuki attachment of the upper fluoroalkenyl side chains required the use of a latent alkene in the lower chain. Double fluoroalkene ring-closing metathesis installed two outer six-membered rings simultaneously. Final double dehydroaromatization was achieved using trityl tetrafluoroborate.
More Related Videos
Related Concept Videos
Thermal and Photochemical Electrocyclic Reactions: Overview
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Cycloaddition Reactions: Overview

