99984-38-0Relevant articles and documents
Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
Boichenko, Maksim A.,Andreev, Ivan A.,Chagarovskiy, Alexey O.,Levina, Irina I.,Zhokhov, Sergey S.,Trushkov, Igor V.,Ivanova, Olga A.
, p. 1146 - 1157 (2020)
A straightforward method for ring opening of donor-acceptor cyclopropanes with trimethylsilyl cyanide as a surrogate of cyanide ion in the presence of B(C6F5)3 or trifluoromethanesulfonic acid as a catalyst has been developed. The methodology provides a short route to γ-cyanoesters that can be useful synthetic intermediates for the synthesis of diverse bioactive molecules such as glutaric and δ-aminovaleric acid derivatives, 3-arylpiperidines, or other substituted phenethylamines. Oppositely, the attempts to synthesize these γ-cyanoesters by direct reaction of cyclopropanes with sodium cyanide under typical SN2 conditions led to the formation of 2-arylsuccinonitriles.
