Uncatalized Strecker-type Reaction of N,N-Dialkylhydrazones in Pure Water

Eugenia Marqués-López, Raquel P. Herrera, Rosario Fernández, José María Lassaletta. Uncatalized Strecker-type Reaction of N,N-Dialkylhydrazones in Pure Water. Eur. J. Org. Chem.. 2008, Vol. , p. 3457-2008.

<p>Aldehyde and ketone N,N-dialkylhydrazones behave as a stable class of imine surrogates exhibiting a unique reactivity in the Strecker reaction with in situ generated HCN, that proceeds in pure water in the absence of co-solvents, catalysts or promoters. Experimental evidence suggests that the reaction is assisted by an intramolecular activation of HCN by the dialkyl amino lone pair.</p>