Majji, Ganesh ; Rajamanickam, Suresh ; Khatun, Nilufa ; Santra, Sourav Kumar ; Patel, Bhisma K. (2015) Generation of bis-acyl ketals from esters and benzyl amines under oxidative conditions The Journal of Organic Chemistry, 80 (7). pp. 3440-3446. ISSN 0022-3263
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Official URL: https://pubs.acs.org/doi/abs/10.1021/jo502903d
Related URL: http://dx.doi.org/10.1021/jo502903d
Abstract
Treatment of benzylamines with esters at an elevated temperature are expected to give amides. However, in the presence of TBAI/TBHP, esters possessing a methylene carbon α-to oxygen with benzylamines provide bis-esters rather than the expected amides. Benzylamines under oxidative conditions generate less nucleophilic carboxylates, which couples at the sp3 C–H bonds of esters and cyclic ethers to give bis-acyl ketals and α-acyloxy ethers, respectively.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 113813 |
Deposited On: | 30 Apr 2018 12:19 |
Last Modified: | 30 Apr 2018 12:19 |
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