Ring Opening of Siloxyaryl‐Substituted Donor–Acceptor Cyclopropanes With Acetone Cyanohydrin as a Cyanide Source

ABSTRACT

p ‐Siloxy‐aryl‐substituted donor–acceptor cyclopropanes (DAC) undergo fluoride‐induced ring‐opening cyanation with acetone cyanohydrin serving as a convenient cyanide source. The transformation proceeds in high yields under mild metal‐free conditions. The proposed reaction mechanism was supported by the successful involvement of stable p ‐quinone methide in the desired transformation. o ‐Siloxy‐phenyl‐substituted DAC underwent ring opening with cyanide as well. Subsequent modifications demonstrated the utility of obtained products for the preparation of diarylacetonitrile and piperidone derivatives.