Synthesis

The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazoles

Y Tang, Y Dong, JL Vennerstrom

Index: Tang, Yuanqing; Dong, Yuxiang; Vennerstrom, Jonathan L. Synthesis, 2004 , # 15 p. 2540 - 2544

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Citation Number: 12

Abstract

Abstract The reactions of non-benzylic primary and secondary aliphatic alcohols with carbonyldiimidazole (CDI) afford the corresponding carbamates but not N-alkylimidazoles. For benzylic primary alcohols, formation of N-alkylimidazoles proceeds reasonably at 170 C in several different solvents and occurs by way of the initially formed carbamate. However, under these rather forcing conditions, or even at lower reaction temperatures, elimination ...