Insertion of S2 into Donor-Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides

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.

Automated summary

A facile and efficient route to dithiolanes starting from donor-acceptor cyclopropanes has been developed. Potassium p-toluenethiosulfonate has been established as the optimal reagent for this reaction. The methodology allows for the synthesis of dithiolanes in moderate to good yields with high functional group tolerance.