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Unexpected variations in sites of lithiation of N-(2-methoxybenzyl)- pivalamide

Smith, Keith., El-Hiti, Gamal A. and Hegazy, Amany Saber 2009. Unexpected variations in sites of lithiation of N-(2-methoxybenzyl)- pivalamide. Synlett (14) , pp. 2242-2244. 10.1055/s-0029-1217722

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Directed lithiation of N-(2-methoxybenzyl)pivalamide with two mole equivalents of t-BuLi in anhydrous THF at -78 ˚C followed by reactions with various electrophiles gave ring substitution, but ortho to the methoxy group rather than ortho to the pivaloylaminomethyl group, which was unexpected in view of earlier results reported with n-BuLi.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: N-(2-methoxybenzyl)pivalamide ; directed lithiation ; synthesis ; dilithium intermediate ; electrophile
Additional Information: Letter
Publisher: Georg Thieme Verlag
ISSN: 0936-5214
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 01:56

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