1159092-04-2Relevant academic research and scientific papers
Improved Cope-type hydroamination reactivity of hydrazine derivatives
Loiseau, Francis,Clavette, Christian,Raymond, Michael,Roveda, Jean-Gregoire,Burrell, Alishya,Beauchemin, Andre M.
scheme or table, p. 562 - 564 (2011/03/16)
A systematic investigation on the metal-free, Cope-type hydroamination reactivity of hydrazides and analogues is reported. Optimization of the hydrazide structure resulted in more facile intramolecular reactivity and enabled intermolecular reactions of al
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
