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Isolation and Structures of 1,2,3‐Triazole‐Derived Mesoionic Biscarbenes with Bulky Aromatic Groups
Author(s) -
Iwasaki Haruka,
Yamada Yuji,
Ishikawa Ryuta,
Koga Yuji,
Matsubara Kouki
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501626
Subject(s) - mesoionic , chemistry , carbene , molecule , triazole , crystal structure , aromaticity , acceptor , pincer movement , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , catalysis , physics , condensed matter physics
1,2,3‐Triazole‐derived mesoionic biscarbenes bridged by a pyridylene group were synthesized and their structures were determined. Bulky substituents on the carbene rings stabilized the carbenes, which enabled their crystal structures to be determined. As implied by DFT calculations and the experimental results, the carbenes are partly reduced to anionic radical species in the presence of strong bases. This suggests that the pyridylene and triazolylidene moieties endow molecules with both electron‐acceptor and ‐donor properties. A rare example of an iron complex with a pincer carbene was synthesized.