scholarly journals Stereochemical studies. LX. Neighboring phenyl group participation. I. Stereospecific transformation of L-phenylalanine to optically active tropic acid.

1984 ◽  
Vol 32 (11) ◽  
pp. 4426-4430 ◽  
Author(s):  
TZUOHMIIN JUANG ◽  
SHUNICHI YAMADA
Keyword(s):  
Phenyl Group ◽  
Optically Active ◽  
Group Participation ◽  
Tropic Acid

Optically Active Amines. Part XIII. Circular Dichroism of the N-Salicylidene Derivatives of Alkylamines

1971 ◽  
Vol 49 (17) ◽  
pp. 2902-2906 ◽  
Author(s):  
Howard E. Smith ◽  
Harry E. Ensley
Keyword(s):  
Circular Dichroism ◽  
Phenyl Group ◽  
Electron System ◽  
Optically Active ◽  
Rotational Strength ◽  
Cotton Effects ◽  
Derivatives Of ◽  
Circular Dichroïsm

Comparison of the c.d. spectra of (S)-(+)-N-salicylidene-α-phenylethylamine with those of (S)-(+)-N-salicylidene-sec-butylamine and (R)-(−)-N-salicylidene-2,2-dimethyl-3-aminobutane confirms the conclusion that the strong rotational strength shown by N-salicylidene-α- and β-phenylalkylamines is due to an interaction of the π-electron System of the phenyl group and the salicylidenimino chromophore. The sign of the Cotton effects near 255 and 315 nm shown by the N-salicylidenes of alkylamines and cycloalkylamines, when these are conformationally defined, can be correlated with their absolute configurations using a planar sector rule, similar to that used for the interpretation of the c.d. and o.r.d. spectra of N-salicylidene-α- and β-phenylalkylamines.

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