Synthesis of a Tetraepoxy Nanobelt and Its Reductive Aromatization Attempts

Abstract

Hydrocarbon nanobelts have recently attracted tremendous interest. Herein, we report our recent progress towards the synthesis of a newly designed hydrocarbon nanobelt tetrabenzo[10]cyclacene, which can be regarded as a sidewall fragment of the (10,0) carbon nanotube. The structures of both key intermediates — “U”-shape diepoxy building block and tetraepoxy nanobelt — were confirmed by single-crystal X-ray diffraction. Our preliminary reductive aromatization reactions revealed that a tetrahydrogenated species instead of tetrabenzo[10]cyclacene was formed during this process. Computational results further revealed that hydrogenation can lead to significant strain release of the backbone structure of tetrabenzo[10]cyclacene, which may attribute to the absence of the target compound during the reductive aromatization.

Key words

hydrocarbon nanobelts - reductive aromatization - hydrogenation - strain

Supporting Information

Supporting Information for this article is available online at http://doi.org/10.1055/s-0040-1721101.

Publikationsverlauf

Eingereicht: 13. September 2020

Angenommen: 09. Oktober 2020

Artikel online veröffentlicht:
18. Dezember 2020

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