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Disulfide metathesis via sulfur...iodine interaction and photoswitchability

Mathuri, Ashis, Pramanik, Milan, Parida, Amarchand and Mal, Prasenjit 2021. Disulfide metathesis via sulfur...iodine interaction and photoswitchability. Organic and Biomolecular Chemistry 19 (39) , pp. 8539-8543. 10.1039/D1OB01581H

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The idea of constitutional dynamic chemistry (CDC) and dynamic combinatorial chemistry (DCC) is widespread in the literature using the chemistry of disulfides. The synthesis of unsymmetrical diaryl disulfides is challenging due to the presence of a weak S–S bond. We report herein the synthesis of unsymmetrical diaryl disulfides from two symmetrical disulfides via a cross-metathesis reaction which was controlled by a weak sulfur⋯iodine (S⋯I) interaction. The unsymmetrical disulfides were stable in acetonitrile solution in the presence of N-iodosuccinimide (NIS), and found to be reversibly photoswitchable to the symmetrical disulfides under visible light irradiation.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of Acceptance: 10 September 2021
Last Modified: 24 Jan 2023 10:45

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