Sulfur Compounds, 174. Preparation of Long‐Chain Polysulfanes from Dialkoxysulfanes: Synthesis of Bis(2,3,4,6‐tetra‐ O ‐acetyl‐1‐deoxy‐β‐D‐glucopyranosyl)tetrasulfane and ‐undecasulfane

Dialkoxysulfanes (RO) 2 S n ( n ≥ 2) react with thiols R′SH as sulfur transfer reagents to form long‐chain diorganylpoly‐sulfanes R′ 2 S n +2 under mild conditions. Condensation of tetra‐ O ‐acetyl‐1‐thio‐β‐ D ‐glucopyranose ( ac GlcSH) with diisopropoxydisulfane ( i PrO) 2 S 2 and diisopropoxynonasulfane ( i PrO) 2 S 9 at 40°C yields bis(2,3,4,6‐tetra‐ O ‐acetyl‐1‐deoxy‐β‐ D ‐glucopyranosyl)tetrasulfane ( 1 ) ( ac Glc) 2 S 4 and bis(2,3,4,6‐tetra‐ O ‐acetyl‐1‐deoxy‐β‐ D ‐glucopyranosyl)undecasulfane ( 2 ) ( ac Glc) 2 S 11 , respectively. The analogous reaction using diisopropoxymonosulfane does not yield the corresponding trisulfane.