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Variation in the site of lithiation of 2-(2-Methylphenyl)ethanamine derivatives

Smith, Keith, El-Hiti, Gamal A. and Alshammari, Mohammed 2012. Variation in the site of lithiation of 2-(2-Methylphenyl)ethanamine derivatives. The Journal of Organic Chemistry 77 (24) , pp. 11210-11215. 10.1021/jo3023445

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Unexpectedly, lithiation of N'-(2-(2-methylphenyl)ethyl)-N,N-dimethylurea with three equivalents of n butyllithium in anhydrous THF at 0 C takes place on the nitrogen and on the CH2 next to the 2-methylphenyl ring (α-lithiation). The lithium reagent thus obtained reacts with various electrophiles to give the corresponding substituted derivatives in excellent yields. Similarly, lithiation of N-(2-(2-methylphenyl)ethyl)pivalamide under similar reaction conditions followed by reaction with benzophenone as a representative electrophile gave the corresponding α-substituted product in high yield. Surprisingly, no products resulting from lateral lithiation were observed under the conditions tried, which sharply contrasts with the reported results for lateral lithiation of tert-butyl (2-(2-methylphenyl)ethyl)carbamate.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: The American Chemical Society
ISSN: 0022-3263
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 04:41

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