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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Photochemical Reaction of Vinyldiazo Esters and Azides: Synthesis of β-Oxodiazo Compounds
Jiabao Tian1, Yanan Wang1, JinXiong Zhang1
1School of Chemistry, Sun Yat-Sen University, 135 Xingang West Road, Guangzhou510275, China.
Abstract:
A photochemical diazo transfer strategy has been developed for the synthesis of unusual β-oxodiazo compounds. Vinyldiazo esters generate transient cyclopropene-1-carboxylates upon selective photolysis, which undergo 1,3-dipolar cycloaddition with TMSN3 followed by a retro-1,3-dipolar process to deliver β-diazoimines. Hydrolysis of these intermediates affords a broad range of β-diazoaldehydes and β-diazoketones. The synthetic potential of this underexplored diazo class is further highlighted through diverse transformations of both the carbonyl and diazo functionalities.
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