Synthesis and Characterization of Hexafluorocyclopentane‐Bridged Bisbutatrienes as Models for Longer Cumulenes: Various Transformations for the Construction of π‐Conjugated Frameworks

Author:

Konishi Akihito123ORCID,Imai Shizuka1,Satake Shoya1,Chiba Kouji4,Yasuda Makoto12ORCID

Affiliation:

1. Department of Applied Chemistry Graduate School of Engineering Osaka University 2-1 Yamadaoka Suita Osaka 565-0871 Japan

2. Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI) Osaka University Suita Osaka 565-0871 Japan

3. Center for Atomic and Molecular Technologies Graduate School of Engineering Osaka University 2-1 Yamadaoka Suita Osaka 565-0871 Japan

4. Material Science Division MOLSIS Inc. 3-19-9 Hatchobori Chuo-ku Tokyo 104-0032 Japan

Abstract

AbstractCumulenes have attracted considerable attention due to their unique structural and electronic properties. Despite their high potential for constructing condensed π‐conjugated molecules, the synthetic utility of longer cumulenes remains to be established owing to their inherently high reactivity. Conjugated bisbutatrienes having two cumulene moieties linked by a spacer as a mimic of a longer cumulene were evaluated. Here, the synthesis and characterization of hexafluorocyclopentane‐bridged bisbutatrienes are described. These bisbutatrienes underwent various cyclizations, to construct the unique π‐extended frameworks inaccessible by other methodologies. The bisbutatrienes were converted into fulvenes, pentalene, germacycle, and benzocyclobutene under various conditions. Furthermore, a cyclooctatetraene derivative was synthesized by a one‐step dimerization of the bisbutatriene.

Funder

Japan Society for the Promotion of Science London

Japan Science and Technology Corporation

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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