Oxidation of menthone oxothiolane.

Authors :: Timshina, A. V.
Rubtsova, S. A.
Alekseev, I. N.
Kodess, M. I.
Mamochkina, E. G.
Slepukhin, P. A.
Kuchin, A. V.
Source :: Chemistry of Natural Compounds. Nov2008, Vol. 44 Issue 6, p728-731. 4p. 1 Diagram.
Publication Year :: 2008
Abstract: meta-Chloroperoxybenzoic acid ( m-ClPBA) was shown to be an oxidant for two stereoisomers of menthone oxothiolane. The effect of steric factors on the ability to oxidize the sulfide group was found. Oxidation of (5 S,6 S,9 R)-6-isopropyl-9-methyl-1-oxo-4-thiaspiro[4.5]-decane to the sulfone was prevented by the steric proximity of an isopropyl group to the S atom in the oxothiolane ring. [ABSTRACT FROM AUTHOR]