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Syntheses and Structures of 10‐Trimethylelement‐Substituted 1,8‐Dichloroanthracenes
Author(s) -
Lamm JanHendrik,
Vishnevskiy Yury V.,
Ziemann Eric,
Kinder Timo A.,
Neumann Beate,
Stammler HansGeorg,
Mitzel Norbert W.
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201301383
Subject(s) - chemistry , anthracene , dichloromethane , trimethylsilyl , bromine , crystal structure , nuclear magnetic resonance spectroscopy , mass spectrometry , crystallography , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , solvent , chromatography
1,8‐Dichloroanthracenes bearing EMe 3 substituents at the 10‐position (E = Si, Ge, Sn) have been synthesised by salt elimination reactions. The key compound, 10‐bromo‐1,8‐dichloroanthracene ( 2 ), was quantitatively obtained by conversion of 1,8‐dichloroanthracene with elemental bromine in dichloromethane. The EMe 3 ‐substituted anthracene compounds 1,8‐dichloro‐10‐(trimethylsilyl)‐ ( 3 ), 1,8‐dichloro‐10‐(trimethylgermyl)‐ ( 4 ) and 1,8‐dichloro‐10‐(trimethylstannyl)anthracene ( 5 ) were completely characterised by multinuclear NMR spectroscopy and mass spectrometry. Their molecular structures in the crystalline state were analysed by X‐ray diffraction experiments and compared with the crystal structure of 10‐ tert ‐butyl‐1,8‐dichloroanthracene ( 1 ). It was found that the level of deformation of the anthracene backbone continuously increases along the series of anthracene substituents SnMe 3 < GeMe 3 < SiMe 3 < CMe 3 . Owing to the good agreement of experimental structural parameters with the results of quantum chemical calculations, the molecular deformations can be regarded as inherent molecular properties.