The regioselective α-alkylation of the benzophenone imine of glycinamide, alaninamide, and related derivatives

2006 ◽  
Vol 84 (10) ◽  
pp. 1301-1312 ◽  
Author(s):  
Martin J O'Donnell ◽  
Jeremy D Keeton ◽  
Vien Van Khau ◽  
John C Bollinger

The benzophenone imine of glycinamide was alkylated using ion pair extraction (RX, 10% aq. NaOH, Bu4NHSO4 (1 equiv.), CH2Cl2, rt) to give the α-monosubstituted products, which were then alkylated a second time using stronger basic conditions (KO-t-Bu, THF, 0 °C, RX). Crystal structures of the Schiff bases of glycinamide, an α-monosubstituted and an α,α-disubstituted product were reported.Key words: benzophenone imines, Schiff bases, alkylation, ion pair extraction (IPE), phase-transfer catalysis (PTC), anhydrous base, X-ray crystal structures.




1989 ◽  
Vol 42 (8) ◽  
pp. 1307 ◽  
Author(s):  
BR Dent ◽  
GJ Gainsford

3,4-Dibromotetrahydrothiophen 1,1-dioxide (2) reacts in the reagent system chloroformaqueous sodium hydroxide-benzyltriethylammonium chloride to give 3-dichloromethylene-2,3-dihydrothiophen 1,1-dioxide (6a), for which low-temperature X-ray structural data are presented. Bromoform may be substituted for chloroform to give the corresponding dibromomethylene compound (6b) in good yield.





2020 ◽  
Vol 67 (3) ◽  
pp. 860-865
Author(s):  
Jin-Long Hou ◽  
Hong-Yuan Wu ◽  
Cheng-Bin Sun ◽  
Ye Bi ◽  
Wei Chen


2021 ◽  
pp. 197-228
Author(s):  
Florenci V. González Adelantado


2012 ◽  
Vol 124 (24) ◽  
pp. 6013-6016 ◽  
Author(s):  
Christian Appelt ◽  
J. Chris Slootweg ◽  
Koop Lammertsma ◽  
Werner Uhl


2011 ◽  
Vol 37 (12) ◽  
pp. 935-940 ◽  
Author(s):  
P. Wang ◽  
Q. L. Li ◽  
Q. Ruan ◽  
Y. Q. Su


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