Issue 42, 2015

Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

Abstract

A rhodium complex derived from RhH(PPh3)4, dppe, and 4-ethynyltoluene catalyzes the addition reaction of sulfur to norbornenes giving the corresponding thiiranes under acetone reflux conditions. The rhodium complex effectively transfers a sulfur atom to the double bond from sulfur, and exo-adducts are obtained. The reaction is also applicable to (E)-cyclooctene and cyclic allenes. The ring-opening reaction of the thiiranes with lithium aluminium hydride gives the corresponding thiols.

Graphical abstract: Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

Supplementary files

Article information

Article type
Communication
Submitted
21 Feb 2015
Accepted
17 Apr 2015
First published
17 Apr 2015

Chem. Commun., 2015,51, 8821-8824

Author version available

Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

M. Arisawa, T. Ichikawa and M. Yamaguchi, Chem. Commun., 2015, 51, 8821 DOI: 10.1039/C5CC01570G

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