SULFURIMIDE ANIONS .2. ALKYLATION OF HEPTASULFURIMIDE

The reaction of strong bases with heptasulfurimide in anhydrous tetrahydrofuran leads to proton abstraction in competition with addition of base to sulfur-sulfur and/or sulfur-nitrogen bonds. Proton abstraction, leading to the heptasulfurimide anion, is favored at low temperatures and by relatively weak bases such as lithium hydroxide. Once formed, the heptasulfurimide anion persists in solution, probably in equilibrium with a small quantity of another species, for days at room temperature and regenerates heptasulfurimide on acidification. The ion effects nucleophilic substitution on primary and secondary but not tertiary alkyl halides giving N-substituted alkyl derivatives of heptasulfurimide. © 1969, American Chemical Society. All rights reserved.