Toward the synthesis of a highly strained hydrocarbon belt.

Hydrocarbon belts including fully conjugated beltarenes and their (partially) saturated analogs have fascinated chemists for decades due to their aesthetic structures, tantalizing properties and potential applications in supramolecular chemistry and carbon nanoscience and nanotechnology. However, synthesis of hydrocarbon belts still remains a formidable challenge. We report in this communication a general approach to hydrocarbon belts and their derivatives. To close up all four fjords of resorcin[4]arene derivatives through multiple intramolecular Friedel-Crafts alkylation reactions in an operationally simple one-pot reaction manner enabled efficient con-struction of octohydrobelt[8]arenes. Synthesis of belt[8]arene from DDQ-oxidized aromatization of octohydrobelt[8]arene under dif-ferent conditions resulted in aromatization and simultaneous [4+2] cycloaddition reactions with DDQ or TCNE to produce selectively tetrahydrobelt[8]arene-DDQ2, tetrahydrobelt[8]arene-TCNE2, and belt[8]arene-DDQ4 adducts. Formation of belt[8]arene, a fully con-jugated hydrocarbon belt, was observed from retro-Diels-Alder reaction of a belt[8]arene-DDQ4 adduct with laser irradiation under MALDI condition. The new and practical synthetic method estab-lished would open an avenue to create belt-shaped molecules from easily available starting materials.