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Synthesis and Ring Strain of a Benzoborirene‐ N ‐Heterocyclic Carbene Adduct
Author(s) -
Hahn Jennifer,
Keck Constanze,
MaichleMössmer Cäcilia,
von Grotthuss Esther,
Ruth Paul Niklas,
Paesch Alexander,
Stalke Dietmar,
Bettinger Holger F.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804629
Subject(s) - adduct , carbene , ring strain , chemistry , lithium (medication) , borane , medicinal chemistry , ring (chemistry) , boron , crystal structure , strain (injury) , crystallography , stereochemistry , organic chemistry , catalysis , endocrinology , medicine
The reduction of an N ‐heterocyclic carbene (1,3‐diisopropyl‐4,5‐dimethylimidazolin‐2‐ylidene, I i PrMe2) adduct of dichloro( ortho ‐bromophenyl)borane by tert ‐butyl lithium at low temperature yields the I i PrMe2adduct A of parent benzoborirene, a highly strained boron‐containing bicyclic compound. A is unstable at room temperature and dimerizes at low temperature to the bis‐I i PrMe2adduct of 9,10‐dihydro‐9,10‐diboraanthracene, characterized by single‐crystal X‐ray crystallography.
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