Antiaromatic compounds: a brief history, applications, and the many ways they escape antiaromaticity

Abstract Beginning from a historical viewpoint, this chapter discusses the evolution of the antiaromaticity concept—covering the early synthetic challenges of preparing cyclobutadiene, orbital symmetry considerations of antiaromaticity, and transformations that convert [4n] π-antiaromatic rings into “aromatic” systems, ending with a brief survey of some applications of antiaromatic compounds.