ADDITION of THIO COMPOUNDS to (R)-LIMONENE CATALYZED by AMBERLYST-15

Abstract

The addition of thioacids and thiophenol to (R)-limonene catalyzed by Amberlyst-15 produced the corresponding 9-thioester- or 9-thioether-p-menthene chemo- and regioselectively.

Keywords:

• Amberlyst-15
• ion-exchange resin
• limonene
• thioether
• thioester

We thank Elizabeth R. Lachter for the kindly donation of Amberlyst-15, andW. Bruce Kover and David E. Nicodem for helpful discussions. AMS thanks CNPq for a fellowship.

Notes

* It is known that limonene produces peroxides quickly.

^a Yield of pure product based on limonene.

^b Limonene recovered.

*As the solvent (CH₂Cl₂) does not efficiently solvate the thiols, the basicity in the gas phase can be assumed to be the same as in solution.