10.6084/m9.figshare.1004792.v3
Panuwat Padungros
Panuwat
Padungros
Alexander Wei
Alexander
Wei
Practical Synthesis of Aromatic Dithiocarbamates
Taylor & Francis Group
2014
synthesis
aromatic
dithiocarbamates
2014-07-07 22:21:06
Journal contribution
https://tandf.figshare.com/articles/journal_contribution/Practical_Synthesis_of_Aromatic_Dithiocarbamates/1004792
<div><p></p><p>Oxidation-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 CS<sub>2</sub>. 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.</p>
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