Premium
Frontispiece: Diazoacetonitrile (N 2 CHCN): A Long Forgotten but Valuable Reagent for Organic Synthesis
Author(s) -
Mykhailiuk Pavel K.,
Koenigs Rene M.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202080164
Subject(s) - reagent , organic synthesis , nitrile , chemistry , combinatorial chemistry , nanotechnology , organic chemistry , catalysis , materials science
An uprising star among the nitrile sources : Diazoacetonitrile (N 2 CHCN) is a small reactive diazoalkane, which was synthesized for the first time back in 1898. In contrast to its close analogue ethyl diazoacetate, diazoacetonitrile found only little interest in synthetic chemistry, which might be in part ascribed to the risks associated with its explosion propensity. However, over the course of the last few years, significant progress for the safe access of this diazoalkane has been made and several recent reports showcase its potential. Protocols for the safe generation of diazoacetonitrile, namely in situ generation and flow synthesis, have been developed and opened up a range of chemical applications of this reagent. In their Minireview on page 89 ff., P. K. Mykhailiuk and R. M. Koenigs discuss the synthetic properties and applications of this valuable reagent.