Generation of bis-Acyl Ketals from Esters and Benzyl Amines Under Oxidative Conditions

Ganesh Majji, Suresh Rajamanickam, Nilufa Khatun, Sourav Kumar Santra and Bhisma K. Patel*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India, Email: pateliitg.ernet.in

G. Majji, S. Rajamanickam, N. Khatun, S. K. Santra, B. K. Patel, J. Org. Chem., 2015, 80, 3440-3446.

DOI: 10.1021/jo502903d

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Abstract

In the presence of TBAI/TBHP, treatment of esters possessing a methylene carbon α-to oxygen with benzylamines provides bis-esters rather than the expected amides. Under these oxidative conditions, benzylamines generate less nucleophilic carboxylates, which couple at sp³ C-H bonds of esters and cyclic ethers to yield bis-acyl ketals and α-acyloxy ethers, respectively.

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Key Words

esters, acylals, TBHP

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ID: J42-Y2015