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Synthesis of a Carbodicyclopropenylidene: A Carbodicarbene based Solely on Carbon
Author(s) -
Pranckevicius Conor,
Liu Liu Leo,
Bertrand Guy,
Stephan Douglas W.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600765
Subject(s) - deprotonation , ligand (biochemistry) , chemistry , carbon fibers , metal , transition metal , crystallography , stereochemistry , nuclear magnetic resonance spectroscopy , organic chemistry , materials science , ion , biochemistry , receptor , composite number , composite material , catalysis
The first carbodicarbene stabilized by flanking cyclopropenylidenes is reported. Tetraphenylcarbodicyclopropenylidene ( 2 ) is accessed by deprotonation of the corresponding triafulvene cyclopropenium salt, and has been spectroscopically characterized in [D 8 ]THF solution at −60 °C. Main‐group and transition‐metal complexes of 2 have been accessed, and have revealed the high sigma donating ability, and exclusive η 1 binding of this neutral all carbon ligand. Variable temperature NMR spectroscopy studies reveal varying degrees of free rotation in the flanking cyclopropenylidene groups of 2 in its coordination compounds.