Neutral 6π and 10π Homoaromatics

Key words

neutral homoaromatics - intramolecular Buchner reaction - dearomatization - photoswitch

Significance

Neutral homoaromatic molecules are considered as a class of veiled species mainly owing to the difficulty inherent to their syntheses, isolation and characterizations. Inspired by the previously studied unstable elassovalene, the authors herein achieve a series of novel neutral homoaromatic hydrocarbons with enhanced stability by reducing the ring strain.

Comment

Facilitated by Cu(hFacac)₂, an intramolecular Buchner dearomatization is performed to afford triasterane, which upon oxidation produces a stable homoaromatic molecule. Interestingly, this homoannulene ester is found to undergo a reversible photochemical rearrangement via [1,11]-sigmatropic shift, thereby switching between the 6π and 10π homoaromatic structures.

Publikationsverlauf

Artikel online veröffentlicht:
11. Mai 2023