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Updated: Jan 2, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
Maksim A Boichenko1, Ivan A Andreev2,3, Alexey O Chagarovskiy2,3
1Department of Chemistry , M. V. Lomonosov Moscow State University , Leninskie gory 1-3 , Moscow 119991 , Russian Federation.
Abstract:
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.
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