Date of Award
1976
Document Type
Thesis
Publication Status
Version of Record
Submission Date
October 2026
Thesis/Dissertation Advisor [Chair]
Bieber, Theodore I.
Abstract
The acid-catalyzed N-alkylation of an amide by an alcohol or an alkene occurs successfully if the intermediate carbenium ion is highly stabilized and therefore readily formed. This is because carbenium ion formation must compete successfully with protonation and consequent deactivation of the amide. The carbenium ion will N-alkylate the amide unless steric requirements preclude such attack. In boiling glacial acetic acid acetamide is N-alkylated readily by ferrocenylmethanol, a-hydroxyethylferrocene and vinylferrocene but slowly by triphenylmethanol. Triphenylnmethylation is accelerated by a small amount of sulfuric acid. Reaction of acetamide with diphenylmethanol in boiling glacial acetic acid yields N-diphenylmethylacetamide in the presence of sulfuric acid, diphenylmethyl acetate in the ascence of sulfuric acid. Under both these conditions the reaction of acetamide with benzyl alcohol fails, benzyl acetate being the sole product. Nicotinamide is triphenylmethylated and ferrocenylmethylated only on the amide nitrogen, not on the pyridine nitrogen. N-methylacetamide, a secondary amide, can be N-ferrocenylmethylated.
Extent
187 p.
Recommended Citation
BROWN, PATRICK MARTIN, "N-ALKYLATION OF AMIDES USING ALCOHOLS OR ALKENES" (1976). Electronic Theses and Dissertations 1970 - 1979. 481.
https://digitalcommons.fau.edu/etd_general_2/481
Identifier
FADT13786
Comments
Thesis (M.S.)--Florida Atlantic University, 1976.|Charles E. Schmidt College of Science|FAU Electronic Theses and Dissertations Collection|Thesis (M.S.)--Florida Atlantic University, 1976.