Synthesis of Methanethial S-Oxide (Sulfine) and Alkanethial S,S-Dioxides by Fluorodesilylation. Stereochemistry of Their Cyclopentadiene Diels-Alder Adducts

Article abstract of DOI:10.1016/S0040-4039(00)99062-2

Fluorodesilylation of trimethylsilylmethanesulfinyl chloride 4 in the presence of cyclopentadiene gives 2-thiabicyclo<2.2.1>hept-5-ene endo-2-oxide, 5; in a like manner 1-trimethylsilylalkanesulfonic anhydrides afford endo- and exo-3-alkyl-2-thiabicyclo<2.2.1>hept-5-ene 2,2-dioxides, with the endo isomer predominating.Sulfine and alkyl sulfenes are invoked.