The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes

Abstract

A simple redox bistable system is available in one step from a stable carbene and a bis(acyl chloride).

Soluble, crystalline, and thermally stable alkali CO2− and carbonite (CO22−) clusters supported by cyclic(alkyl)(amino) carbenes

“… 6 Notably, the ambiphilic nature of stable singlet carbenes has allowed the development of a rich body of organic chemistry which is distinct from their utility in metal-based systems. 7 In such transformations, a common reaction step involves the carbene functioning as a neutral carbon nucleophile with the desired electrophilic substrate(s). A significant example of this class of reaction is the behavior of free carbenes in the presence of CO 2 , where the carbene lone pair forms a covalent bond with the electrophilic carbon atom of CO 2 .…”

Highly Stable 1,2-Dicarbonyl Radical Cations Derived from N-Heterocyclic Carbenes

“…Stable singlet carbenes − are well known to facilitate the generation and utilization of unstable species, − such as main group and organic radicals, including carbonyl, − propargyl, − and aminyl , derivatives. In this context, we designed 1,2-dicarbonyl radical cations supported by two N -heterocyclic carbenes (NHCs), which provide steric protection and delocalization of the spin density.…”

Redox-induced reversible [2 + 2] cycloaddition of an etheno-fused diporphyrin

“…Importantly, the redox response of 4b , namely the reversible cycloreversion involving the cleavage of two C–C bonds, is exceptional among dyrex systems. 6,7 Quadricyclane, anthracene-dimer, and acridizinium dimer undergo double C–C bond cleavage upon electron-transfer, providing norbornadiene, anthracene, and acridizinium, respectively. 11–13 In these cases, however, the reverse C–C bond formation requires light-irradiation.…”