Insertion of S<sub>2</sub> into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides
Anu Jacob, Philip Barkawitz, Peter G. Jones, Daniel B. Werz
Abstract
A facile and efficient route to dithiolanes starting from donor–acceptor cyclopropanes is reported. Potassium p-toluenethiosulfonate has been established as the reagent of choice for this formal insertion of the disulfide moiety. Using this methodology, dithiolanes have been synthesized in moderate to good yields with high functional group tolerance. Upon treatment with an excess of mCPBA, the corresponding dithiolanes delivered four-membered thietane dioxides, the formal (3+1)-cycloaddition product of D–A cyclopropanes, and sulfur dioxide.
Topics & Concepts
ChemistryMoietyCycloadditionAcceptorReagentMedicinal chemistryCarbon disulfideSulfurCombinatorial chemistryOrganic chemistryCatalysisPhysicsCondensed matter physicsCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesOrganic Chemistry Cycloaddition Reactions