Synthesis of a labile CAAC-based diazoalkene: formation of a C₄-cumulene and a head-to-tail dimer.

Authors

Vasu Malhotra, Arindam Mal, Priyanka Sarkar, Ramapada Dolai, Siva Sankar Murthy Bandaru, Cem B Yildiz, Carola Schulzke, Anukul Jana

Published in

Dalton transactions (Cambridge, England : 2003). Oct 19, 2026. Epub Oct 19, 2026.

Abstract

Herein, we report the synthesis of a cyclic (alkyl)(amino)carbene (CAAC)-based diazoalkene from the reaction of NHC/CAAC-based carbodicarbene with nitrous oxide. In contrast to the previously reported mesoionic N-heterocyclic carbene (mNHC)- and N-heterocyclic carbene (NHC)-based analogues, this CAAC-based diazoalkene is kinetically labile at room temperature and undergoes gradual conversion to a C₄-cumulene. The lability is potentially attributed to the stronger π-accepting character of the CAAC motif relative to that of the NHC. The formation of the CAAC-based diazoalkene is evidenced by its head-to-tail dimerization upon treatment with MeOH. This study reveals the profound difference in the influence of carbene motifs, NHC versus CAAC, on the stability of carbene-based diazoalkenes.

PMID:
42895361
Bibliographic data and abstract were imported from PubMed on 19 Oct 2026.

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