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Synfacts 2023; 19(06): 0553
DOI: 10.1055/s-0042-1751905
Synthesis of Materials and Unnatural Products

Neutral 6π and 10π Homoaromatics

Contributor(s):
Dahui Zhao
,
Jianjun Han
Ngoc TT, Grabicki N, Irran E, Dumele O, *, Teichert JF. * Technische Universität Chemnitz, Humboldt-Universität zu Berlin and IRIS Adlershof, Germany
Photoswitching Neutral Homoaromatic Hydrocarbons.

Nat. Chem. 2023;
15: 377-385
DOI: 10.1038/s41557-022-01121-w.
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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.


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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.


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Publication History

Article published online:
11 May 2023

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