Journal of the Brazilian Chemical Society
versión impresa ISSN 0103-5053
MATTOS, Marcio C. S. de y BERNINI, Rafael Berrelho. The reaction of (R)-limonene with S-thioacids. J. Braz. Chem. Soc. [online]. 2007, vol.18, n.5, pp. 1068-1072. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532007000500029.
The reaction of (R)-limonene with equimolar amount of S-thioacetic or S-thiobenzoic acids in refluxing toluene proceeded regioselectively in anti-Markovnikoff fashion forming 9-[(4R, 8RS)-p-menthenyl] S-thiocarboxylates (71 and 61% yield, respectively). The montmorillonite K-10 clay-catalyzed reaction of (R)-limonene with S-thioacetic acid led to the S-thioester (65%) along with p-menthadienes and p-cymene. It was observed that K-10 clay promoted the isomerization of limonene to p-menthadienes and further disproportionation to p-cymene.
Palabras llave : (R)-limonene; S-thioester; montmorillonite K-10.