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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
chemistry
Variation in the site of lithiation of 2-(2-methylphenyl)ethanamine derivatives
Journal of Organic Chemistry, Volume 77, No. 24, Year 2012
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Description
Unexpectedly, lithiation of N′-(2-(2-methylphenyl)ethyl)-N,N- dimethylurea with 3 equiv 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. © 2012 American Chemical Society.
Authors & Co-Authors
Smith, Keith
United Kingdom, Cardiff
Cardiff University
El-Hiti, Gamal A.
United Kingdom, Cardiff
Cardiff University
Egypt, Tanta
Faculty of Science
Alshammari, Mohammed B.
United Kingdom, Cardiff
Cardiff University
Statistics
Citations: 23
Authors: 3
Affiliations: 2
Identifiers
Doi:
10.1021/jo3023445
ISSN:
00223263
e-ISSN:
15206904