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α-Xanthylmethyl Ketones from α-Diazo ketones

Pedro López-Mendoza, Luis D. Miranda*

*Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior S. N., Ciudad Universitaria, Coyoacán, Ciudad de México, 04510, México, Email: lmirandaunam.com

P. López-Mendoza, L. D. Miranda, Synthesis, 2021, 53, 3777-3790.

DOI: 10.1055/a-1513-9968


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Abstract

A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones proceeds through a protonation/nucleophilic substitution sequence in the presence of p-toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. The reaction provides a broad variety of xanthates.


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Key Words

xanthates, α-diazo ketones, α-xanthylmethyl ketones, free radicals, nucleophilic substitution


ID: J66-Y2021