Möbius;helicene;Alkyne Metathesis

Kinetic Control in the Synthesis of a Möbius Tris((ethynyl)[5]helicene) Macrocycle Using Alkyne Metathesis

The synthesis of conjugated Möbius molecules remains elusive since twisted and macrocyclic structures are low entropy species sporting their own synthetic challenges. Here we report the synthesis of a Möbius macrocycle in 84% yield from the alkyne metathesis of 2,13-bispropynyl[5]helicene. MALDI-MS, NMR, and X-ray diffraction indicated a trimeric product of two-fold symmetry with PPM/MMP configurations in the helicene subunits.