The reaction of primary aromatic amines with alkylene carbonates for the selective synthesis of bis-N-(2-hydroxy) alkylanilines: the catalytic effect of phosphonium- …

M Selva, M Fabris, V Lucchini, A Perosa…

Index: Selva, Maurizio; Fabris, Massimo; Lucchini, Vittorio; Perosa, Alvise; Noe, Marco Organic and Biomolecular Chemistry, 2010 , vol. 8, # 22 p. 5187 - 5198

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Citation Number: 24

Abstract

At T≥ 140° C, different primary aromatic amines (pX–C6H4NH2; X= H, OCH3, CH3, Cl) react with both ethylene-and propylene-carbonates to yield a chemoselective N-alkylation process: bis-N-(2-hydroxyalkyl) anilines [pX–C6H4N (CH2CH (R) OH) 2; R= H, CH3] are the major products and the competitive formation of carbamates is substantially ruled out. At 140° C, under solventless conditions, the model reaction of aniline with ethylene ...