Is the 2,3-carbon–carbon bond of indole really inert to oxidative cleavage by Oxone? – Synthesis of isatoic anhydrides from indoles†,10.1039/C3OB41802B

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Is the 2,3-carbon–carbon bond of indole really inert to oxidative cleavage by Oxone? – Synthesis of isatoic anhydrides from indoles†

Amber C. Nelson,Emily S. Kalinowski,Nikolas J. Czerniecki,Taylor L. Jacobson,Peter Grundt

Organic & Biomolecular Chemistry Pub Date : 10/03/2013 00:00:00 , DOI:10.1039/C3OB41802B

Abstract

A recent report has indicated that the oxidizing agent Oxone does not possess the ability to cleave the 2,3-carbon–carbon bond of indole. Work in our laboratory shows that this is not the case. Indole and a variety of aryl ring substituted derivatives readily react to form synthetically important isatoic anhydrides.