The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or a decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different reaction conditions. The use of solid Cs2CO3 leads unexpectedly to the synthesis of new D-A cyclopropane derivatives via a decyanation reaction, followed by diastereoselective acetylation, whereas the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, the use of tailored reaction conditions allows one to obtain either cyclic or open-chain products in moderate to good yields.

Bisag G.D., Viola P., Bernardi L., Fochi M. (2023). Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction. CATALYSTS, 13(4), 1-20 [10.3390/catal13040760].

Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction

Bisag G. D.;Bernardi L.
;
Fochi M.
2023

Abstract

The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or a decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different reaction conditions. The use of solid Cs2CO3 leads unexpectedly to the synthesis of new D-A cyclopropane derivatives via a decyanation reaction, followed by diastereoselective acetylation, whereas the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, the use of tailored reaction conditions allows one to obtain either cyclic or open-chain products in moderate to good yields.
2023
Bisag G.D., Viola P., Bernardi L., Fochi M. (2023). Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction. CATALYSTS, 13(4), 1-20 [10.3390/catal13040760].
Bisag G.D.; Viola P.; Bernardi L.; Fochi M.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/954148
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