Selective Sodium Borohydride Reductions in Aqueous Dimethylformamide Solution. Neighboring Group Effects in the Cortical Side Chain1

1959 ◽  
Vol 81 (13) ◽  
pp. 3291-3294 ◽  
Author(s):  
D. Taub ◽  
R. D. Hoffsommer ◽  
N. L. Wendler
Keyword(s):  
Sodium Borohydride ◽  
Neighboring Group ◽  
Dimethylformamide Solution ◽  
Group Effects

ChemInform Abstract: NEIGHBORING GROUP EFFECTS IN EPOXIDE RING OPENING, CIS-EPOXY-ALCOHOLS

1976 ◽  
Vol 7 (42) ◽  
pp. no-no
Author(s):  
ERWIN GLOTTER ◽  
PNINA KRINSKY ◽  
MIRIAM REJTOE ◽  
MARTIN WEISSENBERG
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Neighboring Group ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols ◽  
Group Effects

Neighboring-group effects in the reactivities of hydroxyl groups in d-glucopyranosides

1972 ◽  
Vol 21 (3) ◽  
pp. 357-367 ◽  
Author(s):  
E.J. Roberts ◽  
C.P. Wade ◽  
S.P. Rowland
Keyword(s):  
Hydroxyl Groups ◽  
Neighboring Group ◽  
Group Effects

Nachbargruppeneffekte bei der Aminolyse von Estern, II Die Aminolyse von 2-(2-Hydroxybenzyl)phenylacetaten / Neighboring Group Effects in the Aminolysis of Esters, II The Aminolysis of 2-(2-Hydroxybenzyl)phenylacetates

1978 ◽  
Vol 33 (4) ◽  
pp. 439-449 ◽  
Author(s):  
Volker Böhmer ◽  
Klaus Wörsdörfer
Keyword(s):  
Second Order ◽  
Phenyl Acetate ◽  
Third Order ◽  
Neighboring Group ◽  
Rate Law ◽  
Order Rate ◽  
Methyl Phenyl ◽  
Group Effects

Abstract The aminolysis of 2-(2-hydroxybenzyl)phenyl acetates with n-butylamine in dioxane is much faster than for the corresponding 2-(2-methoxybenzyl)phenyl acetates or 2-methyl-phenyl acetates. The kinetic results can be explained by two equivalent mechanisms. Both of them include the formation of a 1:1-complex between 2-(2-hydroxybenzyl)phenyl acetate and n-butylamine which is formed in an equilibrium. The reaction of this complex according to a second order rate law seems to be more probable than the reaction of the free ester according to a third order rate law.

Nachbargruppeneffekte bei der Aminolyse von Estern, III. Der verlangsamende Einfluß von Triethylamin bei der Aminolyse von 2-(2-Hydroxybenzyl )phenylacetaten / Neighboring Group Effects in the Aminolysis of Esters, III. The Rate Diminishing Influence of Triethylamine in the Aminolysis of 2-(2-Hydroxybenzyl)phenylacetates

1979 ◽  
Vol 34 (5) ◽  
pp. 720-727 ◽  
Author(s):  
Volker Böhmer ◽  
Klaus Wörsdörfer
Keyword(s):  
Group Effect ◽  
Neighboring Group ◽  
Tetrahedral Intermediate ◽  
Formation Of Complexes ◽  
Group Effects

Abstract The rate of the aminolysis of 2-(2-hydroxybenzyl)phenylacetates with n-butylamine in dioxane is diminished by the addition of triethylamine. This can be quantitatively described by the competitive formation of complexes between monoacetate and n-butylamine or triethylamine, if the assumption is made, that the complex with triethylamine is aminolysed slowly or not at all. The neighboring group effect in aminolysis cannot be explained therefore by a base catalysed decomposition of the tetrahedral intermediate.

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