Synthesis of β -Dihydroxysulfides by Cleavage of Epoxides Using Quaternized Amino-Functionalized Cross-Linked Polyacrylamide as a New Polymeric Phase Transfer Catalyst

Abstract

Poly [N-(2-aminoethyl)acrylamido]trimethyl ammonium halide resin was developed as a new solid-liquid phase transfer catalyst. This quaternized polyacrylamide catalyzed regioselective ring opening of epoxide by Na 2 S to obtain bis[β-hydroxyalkyl]sulfide in high yield under mild conditions.

Sodium Sulfide

“…21 (B) Regioselective Ring Opening of Epoxides: Na 2 S can be applied as a mild sulfur nucleophile for regioselective ring opening of epoxides to give the corresponding bis[b-hydroxyalkyl]sulfides in the presence of poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride resin as a phase-transfer catalyst. 22 The reaction of 2,2-bis(trifluoromethyl)oxiranes with aqueous solution of Na 2 S leads to the formation of S[CH 2 C(CF 3 ) 2 OH] 2 . 23 (C) Divinylsulfides: A convenient and practical method for the direct synthesis of bis(arylvinyl)sulfides by the addition of sodium sulfide to arylacetylenes has been developed.…”

“…22 The reaction of 2,2-bis(trifluoromethyl)oxiranes with aqueous solution of Na 2 S leads to the formation of S[CH 2 C(CF 3 ) 2 OH] 2 .…”