ChemInform Abstract: Studies on the Homodienyl-[1,5]-hydrogen Shift in Vinylaziridines.
β Scribed by Jens Aahman; Peter Somfai
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 29 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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π SIMILAR VOLUMES
The thermal rearrangement of an N-substituted vinylaziridine to the corresponding (Z)-allylic imine, i.e. a homodienyl-[1,5]-hydrogen shift, was studied at different temperatures in the range 40-90 "C. 'H NMR spectroscopy was used to follow the reaction. Rate constants and activation parameters were
Intervention of a Thermal [1,5] Hydrogen Shift. -Heating a solution of (Ia) in toluene does not afford the desired intramolecular Diels-Alder adduct, however itaconate (IIa) is isolated. An analogous thermal [1,5] hydrogen shift takes place in three structurally related alkenyl maleates. -(ALLEN JR.