Diazoacetonitrile (N2CHCN): A Long Forgotten but Valuable Reagent for Organic Synthesis. Issue 1 (15th October 2019)

• Record Type: Journal Article
• Authors: Mykhailiuk, Pavel K.; Koenigs, Rene M.
• Is Part Of: Chemistry. Volume 26:Issue 1(2019)
• Page Start: 89
• Page End: 101
• Publication Date: 2019-10-15
• Subjects: cyano -- cycloaddition -- diazo compounds -- diazoacetonitrile -- heterocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201903335
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Diazoacetonitrile (N2 CHCN) is a small reactive diazoalkane. It has been synthesized for the first time already in 1898 by Theodor Curtius, however, did not gain much recognition in organic synthesis until recently. Only in 2015, after introduction of in situ and flow protocols for the safe generation of diazoacetonitrile, it started gaining popularity. In this minireview, the synthetic properties and applications of this valuable reagent are discussed. Abstract : Long‐forgotten treasure : Diazoacetonitrile was already described in 1898, yet due to its hazards, applications remained scarce. With the introduction of safe methods for its synthesis over the past years, diazoacetonitrile has now become an important reagent for organic synthesis.