《Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates》 was written by Boichenko, Maksim A.; Andreev, Ivan A.; Chagarovskiy, Alexey O.; Levina, Irina I.; Zhokhov, Sergey S.; Trushkov, Igor V.; Ivanova, Olga A.. Computed Properties of C3H9IOS And the article was included in Journal of Organic Chemistry in 2020. The article conveys some information:
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 methodol. provides a short route to gamma-cyanoesters that can be useful synthetic intermediates for the synthesis of diverse bioactive mols. such as glutaric and delta-aminovaleric acid derivatives, 3-arylpiperidines or other substituted phenethylamines. Oppositely, the attempts to synthesize these gamma-cyanoesters by direct reaction of cyclopropanes with sodium cyanide under typical SN2 conditions led to the formation of 2-arylsuccinonitriles. The experimental part of the paper was very detailed, including the reaction process of Trimethylsulfoxonium iodide(cas: 1774-47-6Computed Properties of C3H9IOS)
Trimethylsulfoxonium iodide(cas: 1774-47-6) is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.Computed Properties of C3H9IOS
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com