Uncatalyzed Strecker-Type Reaction of N,N-Dialkylhydrazones in Pure Water

4 páginas, 2 tablas, 3 esquemas.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.We thank the Spanish Ministerio de Ciencia y Tecnología (grants CTQ2007-61915, CTQ2007-60244, and predoctoral fellowship to E. M.-L.) and the Junta de Andalucía (2005/FQM-658) for financial support. R. P. H. thanks the Consejo Superior de Investigaciones Científicas for a postdoctoral contract.Peer reviewe