The synthesis and chlorinolysis of 5-phenyl-2,4,5-trithiapentane-2,2-dioxide

Abstract

Application of mercaptide anions to the dechlorination of an α-polychlorosulfonyl substrate has provided the key step in a successful synthesis of the title compound. 5-Phenyl-2,4,5-trithiapentane-2,2-dioxide undergoes chlorinolysis in an aqueous medium to yield products consistent with the view that α-sulfonyl oxodichlorosulfonium chlorides and α-sulfonyl dichlorosulfonium chlorides may undergo unusually facile Pummerer rearrangements.

Mechanisms in the chlorinolysis of sulfinyl chlorides

“…Chlorinolysis of 3c, as w e have pointed out (2), is very likely to produce 3a and does furnish the sulfone-sulfonyl chloride 2 as we had hoped.…”

Optimizing disulfide fungitoxicity: Adjustment of hydrocarbon chain length

“…Our synthesis of the first a-sulfone disulfide [8] required six steps from dimethyl sulfoxide. We have, subsequently, developed a much more efficient approach [2] which employs reactions of a-ester disulfides with sulfinic acid salts (see Sch.…”

“…Finally, our preparation of the a-sulfone disulfide 13 exploited the approach we first developed for a-mesyl disulfides [8] (see Sch. 10).…”

“…CH 3 SO 2 CCl 2 SOCH 3 [8] (0.56 g, 2.49 mmol) was added and the reaction mixture stirred at ambient temperature for 2.5 days.…”

Synthesis and X-ray crystal structures of selected ω-mercaptosulfones

“…Access to the starting material was provided by permanganate oxidation of dimethyl disulfide in propionic acid solution [20]. Deprotection of the α-sulfone disulfide, as shown in scheme 1, is a delicate step which was carried out by means of benzenethiol in methylene chloride employing a catalytic amount of pyridine [2,4]. SCHEME 1…”