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Issue 2, 2019
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Trichalcogenasumanenes containing various chalcogen atoms: synthesis, structure, properties, and chemical reactivity

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Abstract

Trichalcogenasumanenes (1–3) are rich in chemistry, as they can be regio-selectively functionalized. Chalcogen atoms (S, Se, and Te) play a pivotal role in determining molecular geometry, optical properties, and reactivity. Herein, new trichalcogenasumanenes (4–9) are synthesized, all with the benzylic carbons on sumanene replaced by two kinds of chalcogen atom. Crystallographic studies show that the molecular geometry varies from bowl-shaped (4 and 6) to planar (9) as the size of the majority chalcogen atom increases from S (4) to Se (6) to Te (9). The optical properties of sulfur-rich (4–5), selenium-rich (6–7), and tellurium-rich (8–9) examples are respectively similar to those of trithia- (1), triselena- (2), and tritellura-sumanenes (3). The chemical activities of 4–7 are evaluated via reactions with Oxone, H2O2, and Br2. It is found that their reactivities are dominated by the heavier chalcogen atom rather than the one in the majority.

Graphical abstract: Trichalcogenasumanenes containing various chalcogen atoms: synthesis, structure, properties, and chemical reactivity

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Publication details

The article was received on 10 Nov 2018, accepted on 04 Dec 2018 and first published on 05 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01220B
Citation: Org. Chem. Front., 2019,6, 263-272

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    Trichalcogenasumanenes containing various chalcogen atoms: synthesis, structure, properties, and chemical reactivity

    S. Wang, J. Shang, C. Yan, W. Wang, C. Yuan, H. Zhang and X. Shao, Org. Chem. Front., 2019, 6, 263
    DOI: 10.1039/C8QO01220B

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