Persistent paramagnetic species have found applications in a wide range of fields, including synthetic chemistry (i.e. radical polymerization, oxidative catalysis), medicinal chemistry, and material sciences. However, the synthesis of stable monomeric carbon-centered radicals has remained difficult when compared to heteroatom based paramagnetic systems. Herein, we demonstrate that monomeric (amino)(carboxy) radicals can be synthesized in two easy steps: the addition of a stable cyclic (alkyl)(amino) carbene to an acyl chloride, followed by a one-electron reduction. The stability of these carbon-centered paramagnetic systems also allows for the synthesis and isolation of related bi- and tri-radicals.

Bottleable (amino)(carboxy) radicals derived from cyclic (alkyl)(amino) carbenes

251st National Meeting (2016)

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