Electronic effects in the acid-promoted deprotection of N-2, 4-dimethoxybenzyl maleimides

DJ Watson, ED Dowdy, WS Li, J Wang, R Polniaszek

Index: Watson, Daniel J.; Dowdy, Eric D.; Li, Wen-Sen; Wang, Jianji; Polniaszek, Richard Tetrahedron Letters, 2001 , vol. 42, # 10 p. 1827 - 1830

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Citation Number: 13

Abstract

Cleavage of several 2, 4-dimethoxybenzylmaleimides could be performed employing TFA in anisole. Electronic effects exemplified by varying the substitution present on the maleimide resulted in a variation in the rate of the deprotection. In contrast, 2, 4- dimethoxybenzylsuccinimides were inert to the conditions.