24476-18-4Relevant academic research and scientific papers
Charge-accelerated cope rearrangements of 3-amino-1,5-dienes
Spules, Tara J.,Galpin, Jason D.,Macdonald, Dwight
, p. 247 - 250 (2007/10/02)
The charge-accelerated [3,3] sigmatropic rearrangements of 3-amino-1,5-dienes are considerably more facile than those of the corresponding 3-hydroxy-1,5-dienes, requiring reaction temperatures 85 to 140°C lower.
Fragmentation of Homoallylic Alkoxides. Thermolysis of Potassium 2-Substituted Bicyclooct-5-en-2-alkoxides
Snowden, Roger L.,Schulte-Elte, Karl H.
, p. 2193 - 2202 (2007/10/02)
Thermolysis of the potassium 2-substituted bicyclooct-5-en-2-alkoxides derived from alcohols 2-17 at 90-120 deg C in hexamethylphosphoric triamide affords unsaturated ketones resulting from allylic bond cleavage.The mechanistic and synthetic aspects of this anionic fragmentation are discussed with reference to the formation of 1-(3'-cyclohexenyl)-2-alkanones 18-28 via initial heterolytic C(1),C(2)-bond cleavage in the substrate alkoxide and regioselective, intramolecular protonation of the resultant transient allylic anion.
