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Trichalcogenasumanenes Containing various Chalcogen Atoms: Synthesis, Structure, Property, and Chemical Reactivity

Abstract

Trichalcogenasumanenes (1–3) are rich in chemistry as they can be regio-selectively functionalized. The chalcogen atoms (S, Se, and Te) play pivotal role on molecular geometry, optical property, and reactivity. Herein, the new trichalcogenasumanenes (4–9) are synthesized, and they all have the benzylic carbons on sumanene replaced by two kinds of chalcogen atoms. Crystallographic study shows that molecular geometry varies from bowl-shaped (4 and 6) to planar (9) as the size of chalcogen atom in majority 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) ones are respectively similar to those of trithia- (1), triselena- (2), and tritellura-sumanenes (3). The chemical activities of 4–7 are evaluated by reaction with the Oxone, H2O2, and Br2. It is found that the reactivity of them are dominated by the heavier chalcogen atom rather than the one in the majority.

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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., 2018, Accepted Manuscript
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    Trichalcogenasumanenes Containing various Chalcogen Atoms: Synthesis, Structure, Property, and Chemical Reactivity

    S. Wang, J. Shang, C. Yan, W. Wang, C. Yuan, H. Zhang and X. Shao, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO01220B

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