ChemInform Abstract: RK. VON BROMWASSERSTOFFSAEURE MIT ALKYL‐BETA‐TETRAHYDROPYRANYL‐SULFIDEN

Pummerer rearrangements using chlorotrimethylsilane

“…The three compounds had physical and spectroscopic properties identical with those of authentic samples. (13) with Chloro-trimethy1silane.-Chlorotrimethylsilane (435 mg, 4 mmol) was added to a stirred solution of freshly prepared 2-butylthian-4one S-oxide (13) l 5 (376 mg, 2 mmol) in dichloromethane (30 ml) at room temperature and the resulting mixture was stirred for 15 h. Removal of the solvent under reduced pressure followed by column chromatography (dichloromethane petroleum, 1 : l--+dichloromethane) gave 2-butylthian-4-one (16) '' (41 mg, 13%), 2-butyl-2,3-dihydrothiin-4-one (15) l 7 (51 mg, 15%) and finally 2-butyl-5,6-dihydrothiin-4-one (14) l 7 (165 mg, 49%). These compounds had physical and spectroscopic properties identical with those of authentic samples.…”