Journal of Organic Chemistry p. 8705 - 8711 (2013)
Update date:2022-08-03
Topics:
Zhang, Ningning
Yang, Rui
Zhang-Negrerie, Daisy
Du, Yunfei
Zhao, Kang
Treatment of N-alkoxyamides with NBS in toluene was found to conveniently afford the corresponding carboxylic esters, including those bearing a bulky or long-chain substituent, in satisfactory to excellent yields. This approach not only represents a convenient and economic approach to a direct transformation of an alkoxyamide moiety into the carboxylic ester functional group, via oxidative homocoupling and the subsequent thermal denitrogenation, but also facilitates the synthesis of sterically hindered carboxylic esters.
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