Lateral lithiation and substitution of N'-(2-methylphenyl)-N,N-dimethylurea

Journal Article

Smith, Keith . 2014

• Publication Work Type: Research
• Publication Online URL: http://www.arkat-usa.org/get-file/51451/
• Magazine \ Newspaper: Arkivoc
• Issue Number: 9
• Volume Number: V
• Pages: 365-375

Publication Abstract

Lithiation of N'-(2-methylphenyl)-N,N-dimethylurea with three molar equivalents of tert-butyllithium at -40 to -30 °C takes place on the nitrogen and on the methyl group at position 2 of the phenyl group. The lithium intermediate thus obtained reacts with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.