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

Anu Jacob, Philip Barkawitz, Peter G. Jones and Daniel B. Werz*

*Institute of Organic ChemistryTechnische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany, Email: d.werztu-braunschweig.de

A. Jacob, P. Barkawitz, P. G. Jones, D. B. Werz, Org. Lett., 2022, 24, 3028-3032.

DOI: 10.1021/acs.orglett.2c00967

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Abstract

The reaction of donor-acceptor cyclopropanes with potassium p-toluenethiosulfonate enables a facile and efficient route to dithiolanes in good yields with high functional group tolerance. Upon treatment with an excess of mCPBA, the corresponding dithiolanes delivered four-membered thietane dioxides.

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proposed intermediate

Key Words

S-heterocycles

ID: J54-Y2022