Electrochemical fluorination of ( N,N-dialkylamino)alcohols

Series of amino alcohols including 2-( N,N-dialkylamino)ethanols, 3-( N,N-dimethylamino)propanol and 4-( N,N-dimethylamino)butanol were subjected to electrochemical fluorination. In the case of 2-( N,N-dialkylamino)ethanols, the F-(2- N,N-dialkylamino)acetyl fluorides were obtained in fair to good y...

Full description

Saved in:
Bibliographic Details
Published in:Journal of fluorine chemistry 1999-07, Vol.97 (1), p.229-237
Main Authors: Abe, Takashi, Fukaya, Haruhiko, Hayashi, Eiji, Ono, Taizo, Nishida, Masakazu, Soloshonok, Irina, Okuhara, Kunio
Format: Article
Language:English
Subjects:
Carbonates
Electrochemical fluorination
Ethanolamines
Perfluoroacid fluorides
Propanolamines
Trimethylsilyl ethers
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Series of amino alcohols including 2-( N,N-dialkylamino)ethanols, 3-( N,N-dimethylamino)propanol and 4-( N,N-dimethylamino)butanol were subjected to electrochemical fluorination. In the case of 2-( N,N-dialkylamino)ethanols, the F-(2- N,N-dialkylamino)acetyl fluorides were obtained in fair to good yields. Yields of each target compound were strongly dependent on the kind of the dialkylamino group. Cyclic amines having an N-(2-hydroxylethyl) group afforded the corresponding F-[ N-( c-alkylamino)-substituted acetyl fluorides]. Their yields were generally better than those of acyclic analogs. Several 2-( N,N-dialkylamino)ethanols and 3-( N,N-dimethylamino)propanol were converted into the corresponding trimethylsilylethers, aminoalkyl methyl carbonates and bis-aminoalkyl carbonate, respectively, and they were subjected to fluorination for a comparison of the yield with that obtained from that of the parent aminoalcohol.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(99)00053-6