Unexpected Michael Additions on the Way to 2.3,8.9-Dibenzanthanthrenes with Interesting Structural Properties

The synthesis and properties of a new polycyclic aromatic hydrocarbon containing eight annulated rings and based on the anthanthrene core is described. An unexpected, nucleophile‐dependent Michael addition to a dibenzanthanthrene‐1,7‐dione is found, giving a product with three triisopropylsilylacety...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2016-06, Vol.22 (27), p.9097-9101
Main Authors: Reus, Christian, Lechner, Marc P., Schulze, Matthias, Lungerich, Dominik, Diner, Colin, Gruber, Marco, Stryker, Jeffrey M., Hampel, Frank, Jux, Norbert, Tykwinski, Rik R.
Format: Article
Language:English
Subjects:
acenediones
acenes
anthanthrene
Aromatic compounds
Chemistry
Crystallography
Lithium
organic semiconductors
Polycyclic aromatic hydrocarbons
Synthesis
X-rays
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The synthesis and properties of a new polycyclic aromatic hydrocarbon containing eight annulated rings and based on the anthanthrene core is described. An unexpected, nucleophile‐dependent Michael addition to a dibenzanthanthrene‐1,7‐dione is found, giving a product with three triisopropylsilylacetylene units and a remarkable solid‐state structure (as determined by X‐ray crystallography). Eight is enough: A new polycyclic aromatic hydrocarbon containing eight annulated rings and based on the anthanthrene core is synthesized. The dibenzanthanthrene‐1,7‐dione reacts unexpectedly with aryl and acetylenyl lithium via Michael addition (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201601435