C4 Cumulene and the Corresponding Air-Stable Radical Cation and Dication

A neutral C4 cumulene 1 that includes a cyclic alkyl(amino) carbene (cAAC), its air‐stable radical cation 1.+, and dication 12+ have been synthesized. The redox property of 1.+ was studied by cyclic voltammetry. EPR and theoretical calculations show that the unpaired electron in 1.+ is mainly deloca...

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Published in:Angewandte Chemie International Edition 2014-04, Vol.53 (16), p.4168-4172
Main Authors: Li, Yan, Mondal, Kartik Chandra, Samuel, Prinson P., Zhu, Hongping, Orben, Claudia M., Panneerselvam, Saravanan, Dittrich, Birger, Schwederski, Brigitte, Kaim, Wolfgang, Mondal, Totan, Koley, Debasis, Roesky, Herbert W.
Format: Article
Language:English
Subjects:
cumulenes
cyclic alkyl(amino) carbenes
dications
Electrons
radical ions
theoretical calculations
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Summary:A neutral C4 cumulene 1 that includes a cyclic alkyl(amino) carbene (cAAC), its air‐stable radical cation 1.+, and dication 12+ have been synthesized. The redox property of 1.+ was studied by cyclic voltammetry. EPR and theoretical calculations show that the unpaired electron in 1.+ is mainly delocalized over the central C4 backbone. The commercially available CBr4 is utilized as a source of dicarbon in the cumulene synthesis. Carbons get excited! Commercially available CBr4 is utilized as a source of dicarbon for the preparation of the C4 cumulene that contains a cyclic alkyl(amino) carbene (cAAC). Lithium or potassium is used as a reducing agent. The corresponding air‐stable radical cation and dication of the C4 cumulene were also synthesized and their interconversion was studied by cyclic voltammetry.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201310975