title: PRACTICAL SYNTHESIS OF AROMATIC DITHIOCARBAMATES.
abstract: 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 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.
authors.affiliation: Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
authors.forename: Panuwat
authors.initials: P
authors.lastname: Padungros
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana, USA.
authors.forename: Alexander
authors.initials: A
authors.lastname: Wei
keywords: Benzamide; deprotection; dithiocarbamate; oxidation sensitive