Cyclic (alkyl)(amino) carbenes (CAAC) (A) are highly ambiphilic carbenes that are leading the way in new main group chemistry. The main group analogues of carbenes are not well investigated due to their challenging syntheses. Isoelectronic main group analogues of cyclic (alkyl)(amino) carbenes are accessible from dianions of 2,2-disubstituted 1-phenyl-2-(1-phenylethylidene)hydrazones (B). These five-membered heterocycles (C) feature a quaternary carbon and donating amine adjacent to a low valent main group atom. DFT calculations indicate that the carbene, silylene, and phosphenium compounds are stable. The calculations also indicate that the carbene and silylene analogues are more electrophilic than known species (CAAC and Iwamoto’s silylene respectively).

Accessing main group analogues of cyclic (alkyl)(amino) carbenes (CAACs) from dianionic hydrazones

ACS Spring 2022

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