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Carbene Analogues of Boron Stabilized by Neighboring BB Moieties: Doubly Aromatic Bishomotriboriranides
Author(s) -
Unverzagt Markus,
Subramanian Govindan,
Hofmann Matthias,
von Ragué Schleyer Paul,
Berger Stefan,
Harms Klaus,
Massa Werner,
Berndt Armin
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199714691
Subject(s) - carbene , boron , aromaticity , delocalized electron , chemistry , electron delocalization , ion , crystallography , solid state , stereochemistry , medicinal chemistry , molecule , organic chemistry , catalysis
Delocalization in doubly aromatic compounds: Bishomotriboriranide 1 is the first carbene analogue of boron (a borenate ion) characterized in solution (NMR) and in the solid state (X‐ray). With the 3c–2e π bond and 3c–2e π bond that involves the borenate center of 1 * and the neighboring BB unit, 1 belongs to the class of doubly aromatic compounds. The (hypothetical) classical borenate 1 * without these delocalizations is estimated to be about 90 kcal mol −1 higher in energy than 1 (Dur = 2,3,5,6‐tetramethylphenyl).