Vp. Krasnov et al., NUCLEOPHILIC-SUBSTITUTION OF HALOGEN IN 4-HALOGENATED DERIVATIVES OF GLUTAMIC-ACID .2. STRUCTURAL EFFECTS OF ARYLAMINE AS NUCLEOPHILE, Russian chemical bulletin, 44(4), 1995, pp. 635-638
Kinetics of nucleophilic substitution of halogen in diastereomeric dim
ethyl 4-bromo- and 4-iodoglutamates with ortho-, meta-, and para-subst
ituted anilines was studied by HPLC. The threo-diastereomers of the ha
logenated derivatives react 3-5 times faster than the erythro ones. Th
e structure of the transition state is discussed.