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CAAC‐Based Thiele and Schlenk Hydrocarbons
Author(s) -
Maiti Avijit,
Stubbe Jessica,
Neuman Nicolás I.,
Kalita Pankaj,
Duari Prakash,
Schulzke Carola,
Chandrasekhar Vadapalli,
Sarkar Biprajit,
Jana Anukul
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915802
Subject(s) - chemistry , diradical , dimer , hydrocarbon , alkyl , singlet state , carbene , computational chemistry , stereochemistry , organic chemistry , catalysis , physics , nuclear physics , excited state
Diradicals have been of tremendous interest for over a century ever since the first reports of p ‐ and m ‐phenylene‐bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele's hydrocarbon, a Kekulé diradical, and Schlenk's hydrocarbon, a non‐Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele's hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk's hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head‐to‐tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox‐active organic compounds.