The Journal of Organic Chemistry

Directed Lithiation of 2-Phenyl-and 2-(o-methylphenyl) imidazoline

WJ Houlihan, VA Parrino

Index: Houlihan, William J.; Parrino, Vincent A. Journal of Organic Chemistry, 1982 , vol. 47, # 26 p. 5177 - 5180

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Citation Number: 35

Abstract

Hauser hah reported that N-methylbenzamide'(la) and N-methyl-o-toluamide2 (lb) can undergo deprotonation la, R= H 2a, R= Li b, R= CH, b, R= CH, Li and ortho or benzylic lithiation: respectively, when treated with n-BuLi in an inert ether solvent to form the dilithiated species 2a or 2b. Compounds that undergo dilithiation similar to that for 2a have been reported for benzene derivatives with an ortho CSNHR; S02NHR, 5 CH20H, G S03H ...