Liu, Changqing published the artcileHighly Stereoselective Cationic Cyclization Assisted by a Sulfenyl Group. Scope, Limitation, and Mechanism, Quality Control of 22693-41-0, the publication is Journal of Organic Chemistry (1996), 61(2), 494-502, database is CAplus and MEDLINE.
When 8-acetoxy-2-methyl-9-(phenylthio)-2-nonene (1) was treated with an acid, followed by a base, alkylative cyclization proceeded to give a mixture of 1,2-disubstituted cyclohexanes. The stereochem. of the reaction was only slightly affected by the leaving group and the reaction conditions, such as the temperature, solvent, and acid. However, the bulkiness of the sulfenyl group had a great effect on the stereochem. course of the reaction. High trans selectivity was attained when a derivative of 1 with a bulkier sulfenyl group was used as a substrate. On the other hand, the length and rigidity of the carbon chain of the substrate also had a major effect on the stereochem. of the reaction; a high cis selectivity was observed when a one-carbon-fewer analog of 1 or a derivative with one more double bond in the carbon chain than in 1 was used as the substrate. The reaction proceeded via a 6,5- or 5,5-fused-ring intermediate. The sulfenyl-group-assisted reaction could be a useful method for the stereoselective cyclization of acetates of ¦Á-sulfenylated secondary alcs.
Journal of Organic Chemistry published new progress about 22693-41-0. 22693-41-0 belongs to catalysis-chemistry, auxiliary class Other Functionalization Reagent, name is 2,4,6-Triisopropylbenzenethiol, and the molecular formula is C15H24S, Quality Control of 22693-41-0.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia