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Saturated N‐Heterocyclic Carbene Based Thiele's Hydrocarbon with a Tetrafluorophenylene Linker
Author(s) -
Kundu Gargi,
De Sriman,
Tothadi Srinu,
Das Abhishek,
Koley Debasis,
Sen Sakya S.
Publication year - 2019
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.201904421
Subject(s) - carbene , singlet state , chemistry , crystallography , metal , linker , cleavage (geology) , single crystal , stereochemistry , medicinal chemistry , catalysis , materials science , organic chemistry , physics , operating system , fracture (geology) , computer science , nuclear physics , composite material , excited state
The synthesis of a SIPr [1,3‐bis(2,6‐diisopropylphenyl)‐imidazolin‐2‐ylidene] derived Kekulé diradicaloid with a tetrafluorophenylene spacer ( 3 ) has been described. Two synthetic routes have been reported to access 3 . The cleavage of C−F bond of C 6 F 6 by SIPr in the presence of BF 3 led to double C−F activated compound with two tetrafluoro borate counter anions ( 2 ), which upon reduction by lithium metal afforded 3 . Alternatively, 3 can be directly accessed in one step by reacting SIPr with C 6 F 6 in presence of Mg metal. Compounds 2 and 3 were well characterized spectroscopically and by single‐crystal X‐ray diffraction studies. Experimental and computational studies support the cumulenic closed‐shell singlet state of 3 with a singlet‐triplet energy gap (Δ E S–T ) of 23.7 kcal mol −1 .