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Issue 2, 2016
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An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source

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Abstract

Chemical reactions involving high-pressure acetylene are not easily performed in a standard laboratory setup. The risk of explosion and technical difficulties drastically complicate the equipment and greatly increase the cost. In this study, we propose the replacement of acetylene with calcium carbide, which was successfully utilized to synthesize practically useful vinyl thioesters in accordance with a simple and environmentally benign procedure. The reaction proceeded under mild conditions using a standard laboratory setup. The optimized reaction conditions allowed the selective synthesis of the vinyl thioesters in high yields, and the reaction conditions can be scaled up to synthesize grams of sulfides from inexpensive starting materials.

Graphical abstract: An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source

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Supplementary files

Article information


Submitted
09 Jul 2015
Accepted
03 Aug 2015
First published
04 Aug 2015

Green Chem., 2016,18, 482-486
Article type
Paper

An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source

K. S. Rodygin and V. P. Ananikov, Green Chem., 2016, 18, 482
DOI: 10.1039/C5GC01552A

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