1159092-25-7Relevant articles and documents
Hydrazides as tunable reagents for alkene hydroamination and aminocarbonylation
Roveda, Jean-Gregoire,Clavette, Christian,Hunt, Ashley D.,Gorelsky, Serge I.,Whipp, Christopher J.,Beauchemin, Andre M.
supporting information; experimental part, p. 8740 - 8741 (2009/12/04)
(Chemical Equation Presented) Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230°C), afford intramolecular hydroamination products upon heating at high temperatures (120-235°C). A concerted Cope-type hydroamination event, followed by a hydrazide-mediated proton transfer step of the hydrazinium ylide intermediate, is proposed and supported by DFT calculations. In contrast, a simple modification of the reagent structure (R = Ot-Bu or NH2) favors the formation of aminocarbonylation products at 200°C, and the latter reaction is shown to be stereospecific. Copyright