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Nitroepoxide ring opening with thionucleophiles in water: synthesis of α-xanthyl ketones, β-keto sulfones and β-keto sulfonic acids

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Abstract

Nitroepoxide ring opening with thionucleophiles such as potassium xanthates, sodium aryl sulfinates and sodium bisulfite in water is investigated. It provides a direct and green route for the synthesis of α-xanthyl-α-aryl-2-propanones (P2P-xanthate derivatives), β-keto sulfones and β-keto sulfonic acids. High to excellent yields, performing the reaction in water under catalyst-free conditions, and easy work-up are the main advantages of this protocol.

Graphical abstract: Nitroepoxide ring opening with thionucleophiles in water: synthesis of α-xanthyl ketones, β-keto sulfones and β-keto sulfonic acids

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Article information


Submitted
06 May 2020
Accepted
16 Jun 2020
First published
16 Jun 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Nitroepoxide ring opening with thionucleophiles in water: synthesis of α-xanthyl ketones, β-keto sulfones and β-keto sulfonic acids

E. Badali, H. Rahimzadeh, A. Sharifi, A. Habibi and A. Ziyaei Halimehjani, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00941E

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