Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 25, Pages 8740-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja902558j
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Funding
- University of Ottawa
- CFI
- MRI (Ontario)
- NSERC
- Canadian Society for Chemistry, AstraZeneca Canada, Boehringer Ingelheim (Canada) Ltd.
- Merck Frosst Canada
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Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230 degrees C), afford intramolecular hydroamination products upon heating at high temperatures (120-235 degrees 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 degrees C, and the tatter reaction is shown to be stereospecific.
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