Highly regioselective para-methylthiolation/bridging methylenation of arylamines promoted by NH4I
Aryl methyl thioethers and methylene-bridged arylamines were synthesized via highly regioselective para-methylthiolation/bridging methylenation of arylamines using DMSO as the methylthio or methylene source in the presence of NH4I under metal-free conditions. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields.
Xu, Yinfeng,Cong, Tiantian,Liu, Ping,Sun, Peipei
supporting information
p. 9742 - 9745
(2015/10/05)
Effect of Substituents on the Reaction of Aromatic Amines and Formaldehyde in Acid Medium
The kinetics and mechanism of the condensation of N- and C-substituted aromatic amines with formaldehyde in acid medium have been studied using quantitative TLC technique, and the first order rate constants and relative reactivities calculated.In all cases where para-position is free, 4-aminobenzyl alcohols are the initial products.These undergo condensation with amines to give 4-(4-aminobenzyl)anilines.The effect of substituents on the reactivity of amines has been discussed.
Nayar, Mazhuvadyil R. Gopinathan,Francis, Joseph D.
p. 776 - 780
(2007/10/02)
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