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- Title
Side-Chain Lithiation of N' -(4-Chlorophenethyl)- and N' -(4-Methylphenethyl)- N, N-dimethylureas: Experimental and Theoretical Approaches.
- Authors
Alshammari, Mohammed
- Abstract
α-Lithiation of N' -(4-chlorophenethyl)- and N' -(4-methylphenethyl)- N, N-dimethylureas occurs using t-butyllithium (3.3 molar equivalents) in dry tetrahydrofuran at -60 to 0 °C on NH and on the CH2 next to the aryl ring. The lithium reagents generated in situ are trapped with several electrophiles (benzophenone, cyclohexanone, 2-butanone, 4-anisaldehyde, and benzaldehyde) to afford the corresponding substituted ureas in 79-96% yields. The experimental results were sustained by density functional theory calculations, which show that the side chain on the CH2 adjacent to the aryl ring is the most favorable site for the α -lithiation of N' -(4-chlorophenethyl)- N, N-dimethylurea and N' -(4-methylphenethyl)- N, N-dimethylurea.
- Subjects
LITHIATION; TETRAHYDROFURAN; ELECTROPHILES
- Publication
Arabian Journal for Science & Engineering (Springer Science & Business Media B.V. ), 2018, Vol 43, Issue 1, p171
- ISSN
2193-567X
- Publication type
Article
- DOI
10.1007/s13369-017-2602-3