The ability to alter the HOMO-LUMO gap, and subsequently the attendant reactivity, of N-heterocyclic carbenes (NHCs) via decoration with carbonyl groups has been a topical research endeavor for the last few years. As a part of our contribution to this field, we recently disseminated the synthesis and reactivity of the first free amino-acrylamidocarbene (I ). In that paper, we also compared the reactivity of I  to other carbonyl-functionalized carbenes including the diamidocarbene (DAC) II , the mono-amidoamino carbene (MAAC) III , and the amino-ureido carbene IV . This presentation will focus on our ongoing efforts to understand the electronic properties and reactivities of carbenes I -IV  by interrogating their reactivity with the pnictogen-containing compounds: dichlorophenyl phosphine, white phosphorus, and dichlorophenyl antimony.

Reactivity studies of carbonyl-decorated carbenes with phosphorus- and antimony-containing compounds

245th National Meeting (2013)

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