Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane
Sarah Livesley, Bethany Trueman, Craig M. Robertson, William R. F. Goundry, James A. Morris, Christophe Aïssa
Abstract
Thiols easily react with [1.1.1]propellane to give sulfur-substituted bicyclo[1.1.1]pentanes in radical reactions, but this reactivity is not replicated in the case of heterocyclic thiols. Herein, we address this issue by electrophilically activating [1.1.1]propellane to promote its iodo-sulfenylation with 10 classes of heterocyclic thiols in two protocols that can be conducted on a multigram scale without exclusion of air or moisture.
Topics & Concepts
PropellaneChemistryBicyclic moleculeReactivity (psychology)SulfurOrganic chemistryComputational chemistryAlternative medicineMedicinePathologySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions