We and others have recently shown that the introduction of carbonyl groups into the backbone of N-heterocyclic carbenes (NHCs) greatly enhances the p-acidity of the carbene by lowering the LUMO energy. This modification results in carbenes which can be regarded modest electrophiles and poor nucleophiles. This presentation, will discuss how the unique electronic properties of carbonyl-decorated carbenes (CDCs) alters their reactivity toward chlorinated group 15-element containing compounds. Specific attention will be devoted to the reactions of diamidocarbenes and monoamidoamino carbenes with phosphorus, arsenic, and antimony chlorides including PCl3, AsCl3, SbCl3, PhPCl2 and PhSbCl2. As a part of this discussion will also be new synthetic methodologies that we have developed to overcome some of the limitations regarding the reactivity of CDCs toward group 15 chlorides.

Reactivity studies of carbonyl-decorated carbenes with group 15 element-containing compounds

247th National Meeting (2014)

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