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Expanded Cyclotetrabenzoins

31 July 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Cyclobenzoins are stable and shape-persistent macrocycles which offer promise as components of optoelectronic and porous materials. We report three new cyclotetrabenzoins, derived from biphenyl, naphthalene, and tolane skeletons. Their synthesis relied on the N-heterocyclic carbene-catalyzed benzoin condensation. Isolated as their acetic esters, these compounds are characterized by structures similar in shape, but larger in size than the parent cyclotetrabenzoin. Alkyne groups of the tolane-based cyclotetrabenzoin were post-synthetically functionalized with Co2(CO)6 moieties under mild reaction conditions.

Keywords

macrocycles
benzoin condensation
cyclobenzoin

Supplementary materials

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Compound 3b
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Compound 3d
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2020 Eisterhold Cyclotetrabenzoins OrgLett SupportingInformation
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Version History

Jul 31, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.12739655.v1
D O I: 10.26434/chemrxiv.12739655.v1 [opens in a new tab]

Funding

We acknowledge the support from the US National Science Foundation (award DMR-1904998 to O. Š. M.), the Welch Foundation (award E-1768 to O. Š. M.), the donors of the American Chemical Society Petroleum Research Fund (award ND-58919 to O. Š. M.), and the University of Houston. K. V. K. thanks Deutsche Forschungsgemeinschaft (DFG) for funding under Germany’s Excellence Strategy – 2082/1 – 390761711. P. W. thanks the generous funding from the DFG Collaborative Centre SFB/TRR 88 “3MET” (Project C6). O. Š. M. thanks the Max Kade and Alexander von Humboldt Foundations for supporting his summer stay at the Ruprecht-Karls-Universität in Heidelberg (Germany), during which the collaboration that produced these results was initiated.

Author’s competing interest statement

None.

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