Synthesis of Azo Dyes from Mesoionic Carbenes and Nitrous Oxide

Chemistry : a European Journal
Léonard Y M EymannKay Severin

Abstract

Covalent adducts of imidazole-based mesoionic carbenes and nitrous oxide (N2 O, "laughing gas") can be converted into azo dyes by reaction with arenes in the presence of AlCl3 or HCl. The azo coupling can be achieved with electron-rich aromatic compounds such as mesitylene, trimethoxybenzene, azulene, or dibenzo-18-crown-6. The latter coupling reaction allows for the easy preparation of a colorimetric sensor for potassium or sodium ions. As a putative intermediate of the reaction with acid, we were able to isolate and structurally characterize a rare diazohydroxide. Using imidazolium compounds with two N2 O groups, it was possible to prepare amine-substituted azo dyes or dyes with two azoarene groups attached to the heterocycle. A triazole-based mesoionic carbene was also found to form a stable covalent adduct with N2 O. The adduct could be used to prepare novel azo triazolium dyes in good yields.

References

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Nov 19, 2011·Angewandte Chemie·Alexander G TskhovrebovKay Severin
Jan 27, 2012·Journal of the American Chemical Society·Alexander G TskhovrebovKay Severin
Jun 14, 2013·Journal of the American Chemical Society·Alexander G TskhovrebovKay Severin
Aug 29, 2013·Inorganic Chemistry·Alexander G TskhovrebovKay Severin
Nov 13, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Eileen TheuergartenMatthias Tamm
Nov 26, 2014·Angewandte Chemie·Alexander G TskhovrebovKay Severin
Jun 25, 2015·Chemical Society Reviews·Kay Severin
Dec 10, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Robert RobinsonBrian F Yates
Oct 19, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Rajendra S Ghadwal
Dec 10, 2016·Journal of the American Chemical Society·Léonard Y M EymannKay Severin
Mar 23, 2017·Chemistry : a European Journal·Merle ArrowsmithJens Seufert
Apr 4, 2017·Chemical Communications : Chem Comm·Léonard Y M EymannKay Severin

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Citations

Nov 15, 2018·Chemistry : a European Journal·Yizhu LiuKay Severin
Oct 18, 2019·Journal of the American Chemical Society·Léonard Y M EymannKay Severin
Sep 15, 2018·Inorganic Chemistry·Yizhu LiuKay Severin
Oct 9, 2021·Nature Chemistry·Paul VaravaKay Severin

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