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CC BY-ND-NC 4.0 · SynOpen 2018; 02(01): 0064-0071
DOI: 10.1055/s-0036-1591771
DOI: 10.1055/s-0036-1591771
paper
Synthesis of 3-(Arylthio)propionic Acids from Nonactivated Aryl Iodides and their Use as Odorless Aryl Mercaptan Surrogates
National Research Development and Innovation Office (NN 117633).Further Information
Publication History
Received: 14 November 2017
Accepted after revision: 10 February 2018
Publication Date:
14 March 2018 (online)
Abstract
The reaction of aryl iodides, 3-mercaptopropionic acid, and Cu2O in refluxing pyridine resulted in the formation of 3-(arylthio)propionic acids in good to excellent yield. The latter 3-(arylthio)propionic acids — as novel aryl mercaptan equivalents — gave aryl mercaptans or diaryl disulfides, respectively, on reductive (Na2S) or oxidative (I2) cleavage in alkaline media. The symmetrical disulfides can also be prepared by oxidizing their precursor mercaptans with phenyltrimethylammoniumtribromide in pyridine at ambient temperature.
Key words
3-mercaptopropionic acid - sulfur-transfer reagent - 3-(arylthio)propionic acid - reverse Michael reaction - copper(I) oxideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591771.
- Supporting Information
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