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Sterically Exposed Bromothiophene C-Br Bonds as Structural Warning Signs for Hidden Homocoupling in

Masayuki Wakioka1,2,3, Takeru Hirukawa1,2, Risa Ishizuka3

  • 1Sagami Chemical Research Institute, 2743-1 Hayakawa, Ayase, Kanagawa252-1193, Japan.

ACS Macro Letters
|October 23, 2026
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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