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Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis
André U Augustin1, Marius Busse1, Peter G Jones1
1Institute for Organic Chemistry and ‡Institute for Inorganic and Analytical Chemistry, TU Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
Abstract:
Donor-acceptor cyclopropanes were reacted under Lewis acid catalysis with 3-thioxocyclobutanones as surrogates for disubstituted thioketenes. A broad scope of 2-substituted tetrahydrothiophenes with a semicyclic double bond was obtained under mild conditions with high functional group tolerance and in excellent yield. A sequence of a formal [3 + 2]-cycloaddition followed by the subsequent release of disubstituted ketene is postulated as the mechanism.
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