lsyc_a_894527_sm9091.pdf (1.54 MB)
Practical Synthesis of Aromatic Dithiocarbamates
Version 3 2014-07-07, 22:21
Version 2 2014-07-07, 22:21
Version 1 2014-07-07, 22:21
journal contribution
posted on 2014-07-07, 22:21 authored by Panuwat Padungros, Alexander WeiOxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS2. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. The N,N-diaryl DTCs are stable as alkali salts and can be used to produce densely packed monolayers on gold surfaces.