Reactivity pattern of bis(propargyloxy) disulfides: Tandem rearrangements and cyclizations

Samuel Braverman, Tatiana Pechenick-Azizi, Hugo E. Gottlieb, Milon Sprecher

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


Thirty-five substituted bis(propargyloxy) disulfides were successfully prepared in good to excellent yields, and their reactivity was found to be strongly dependent on the substitution pattern of the reactant. Inter alia they undergo surprising tandem sigmatropic rearrangements and cycloadditions. Three heretofore unknown product types were isolated and fully characterized: 6,7-dithiabicyclo[3.1.1]heptan-2-one 6-oxide derivatives, two isomeric 1,2-dithiete 1,1-dioxides (α,β-unsaturated four-membered cyclic thiosulfonates) from bis(propargyloxy) disulfides with α- or γ-alkyl-substituted propargyl groups, and two isomeric 2-oxa-5,7-dithiabicyclo[2.2.1]heptane 5-oxides from bis(propargyloxy) disulfides with α-tert-butyl- or α,α-dialkyl-substituted propargyl groups.

Original languageEnglish
Pages (from-to)1741-1750
Number of pages10
Issue number11
StatePublished - 2011


  • bis(propargyloxy) disulfides
  • cycloadditions
  • dithiabicyclic structures
  • organosulfur chemistry
  • sigmatropic rearrangements
  • substituent effects
  • thiosulfonates
  • vic -disulfoxides


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