Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 16
747
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Practical Synthesis of Aromatic Dithiocarbamates

&
Pages 2336-2343 | Received 15 Jan 2014, Published online: 13 Jun 2014
 

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.

GRAPHICAL ABSTRACT

Notes

a Conversion determined by 1H NMR.

b Isolated yield.

a 1.0–2.5 equiv.

b Isolated yields unless stated otherwise.

c Hydrochloride salt, neutralized with one equivalent of n-BuLi or dimsyl-Li.

d Reaction conditions: (i) 50 °C for 5 h, then −78 °C; (ii) CS2 (5–10 equiv), warmed to rt.

e Yield after a single precipitation.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.