Suppressing the Anionic Fries Rearrangement of Aryl Dialkylcarbamates; the Isolation of a Crystalline ortho??Deprotonated Carbamate

…, JV Morey, D Nobuto, Y Kondo, H Naka…

Index: Garcia, Felipe; McPartlin, Mary; Morey, James V.; Nobuto, Daisuke; Kondo, Yoshinori; Naka, Hiroshi; Uchiyama, Masanobu; Wheatley, Andrew E. H. European Journal of Organic Chemistry, 2008 , # 4 p. 644 - 647

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Citation Number: 13

Abstract

Abstract In the presence of organolithium bases phenyl dialkylcarbamates have previously been shown to undergo facile rearrangement to yield the corresponding salicylamides. However, heterometallic lithium diethyl (2, 2, 6, 6-tetramethylpiperidido) zincate achieves the clean directed ortho-metallation (DoM) of phenyl dialkylcarbamates, with [C 6 H 4 {OC (O) NMe 2}{Zn (-TMP) Et} Li] 2 having been structurally characterized. DFT studies point to a ...

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