Reactions of sulfur halides with unsaturated compounds. 26. Reactions of sulfur dichloride with tricyclo[4.2.2.02,5]deca-3,7-dienes and tricyclo[4.2.2.02,5]deca-3,7,9-trienes. Synthesis of compounds with a novel thiaskeletal structure

Abstract

Addition of sulfur dichloride to tricyclo[4.2.2.02, 5]deca-3,7-dienes and tricyclo[4.2.2.02,5] deca-3,7,9-trienes is accompanied by intramolecular cyclization to give high yields of adducts with the novel thiaskeletal 7-thiatetracyclo[4.2.2.04,8.05,10]undecane structure. In the reaction of SCl2 with the 2,3-endo, endo-diester (V), intramolecular cyclization is accompanied by lactonization, to give quantitative yields of the thiaskeletal chlorolactone (X). The structure of the latter compounds was established by x-ray diffraction examination.