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7450229 
Journal Article 
The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazoles 
Tang, YQ; Dong, YX; Vennerstrom, JL 
2004 
1 
Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 
GEORG THIEME VERLAG KG 
STUTTGART 
15 
2540-2544 
English 
WOS:000224653800019 
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 degreesC 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 is a significant side reaction for benzylic secondary alcohols with beta-hydrogen atoms. With one exception, reactions of six N,N-disubstituted beta-aminoalcohols with CDI to form N-alkylimidazoles proceed under relatively mild conditions and may occur by way of an aziridinium intermediate. 
alcohols; alkylations; carbonyldiimidazole (CDI); carbamates; N-alkylimidazoles 
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