Journal of the American Chemical Society

Effect of nucleophile basicity on intramolecular nucleophilic aminolysis reactions of carbonate diesters

TH Fife, JEC Hutchins

Index: Fife, Thomas H.; Hutchins, J. E. C. Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4194 - 4199

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Citation Number: 26

Abstract

Method B. The lactam (10 mmol) was converted as described above into the imino ether in quantitative yield, which was treated with 3-bromopropylamine hydrobromide (1 1 mmol) in absolute ethanol (15 mL) at 25" C. Stirring was continued at 25" C for 40 h. Then powdered potassium carbonate (22 mmol) was added at 0" C and the whole mixture was stirred at 0" C for 150 min. Dilution with chloroform (300 mL), filtration, and washing of the residue with ...