CATALYSIS OF ALPHA-HYDROGEN EXCHANGE .9. ISOBUTYRALDEHYDE-2-D EXCHANGE IN PRESENCE OF AMINO ACIDS

被引:9
作者
HINE, J
MENON, BC
MULDERS, J
FLACHSKA.RL
机构
[1] Department of Chemistry, Ohio State University, Columbus
[2] School of Chemistry, Georgia Institute of Technology, Atlanta
关键词
D O I
10.1021/jo01264a070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalysis of the deuterium exchange of isobutyraldehyde-2-d by glycine, β-alanine, γ-ammobutyric acid, δ- aminovaleric acid, and ϵ-aminocaproic acid has been studied in the presence of pyridine and acetate buffers. In all cases there appears to be catalysis due to the reversible formation of an iminium ion from the aldehyde and amino acid followed by the removal of deuterium from the iminium ion by the various bases present. In no case could bimolecular catalysis via the internal attack of the carboxylate anion group be established. © 1969, American Chemical Society. All rights reserved.
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页码:4083 / &
相关论文
共 13 条
[1]  
Duggan Edward L., 1943, ARCH BIOCHEM, V1, P453
[2]  
HARNED HS, 1958, PHYSICAL CHEMISTRY E, P676
[3]   CATALYSIS OF ALPHA-HYDROGEN EXCHANGE .I. REACTION OF ISOBUTYRALDEHYDE-2-D WITH TERTIARY AMINES AND OXYGEN BASES [J].
HINE, J ;
HOUSTON, JG ;
JENSEN, JH ;
MULDERS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (22) :5050-&
[4]   CATALYSIS OF ALPHA-HYDROGEN EXCHANGE .7. ISOBUTYRALDEHYDE-2-D EXCHANGE IN PRESENCE OF PRIMARY AMINE SALTS AND PYRIDIME BUFFERS [J].
HINE, J ;
MENON, BC ;
MULDERS, J ;
IDOUX, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12) :3850-&
[5]   CATALYSIS OF ALPHA-HYDROGEN EXCHANGE .6. ISOBUTYRALDEHYDE-2-D EXCHANGE IN PRESENCE OF METHYLAMMONIUM IONS AND VARIOUS BUFFERS [J].
HINE, J ;
MULDERS, J ;
HOUSTON, JG ;
IDOUX, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (07) :2205-&
[7]   CATALYSIS OF ALPHA-HYDROGEN EXCHANGE .2. ISOBUTYRALDEHYDE-2-D EXCHANGE VIA N-METHYLIMINIUM ION FORMATION [J].
HINE, J ;
MENON, BC ;
JENSEN, JH ;
MULDERS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3367-&
[8]   CATALYSIS OF ALPHA-HYDROGEN EXCHANGE .3. EXCHANGE OF ISOBUTYRALDEHYDE-2-D IN PRESENCE OF METHYLAMMONIUM IONS [J].
HINE, J ;
KOKESH, FC ;
HAMPTON, KG ;
MULDERS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (05) :1205-&
[9]   BIFUNCTIONAL CATALYSIS OF DEDEUTERATION OF ISOBUTYRALDEHYDE-2-D BY POLYETHYLENIMINES [J].
HINE, J ;
ROGERS, FE ;
NOTARI, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (12) :3279-&