24480-94-2Relevant academic research and scientific papers
Fragmentation of Homoallylic Alkoxides. Thermolysis of Potassium 2-Substituted Bicyclooct-5-en-2-alkoxides
Snowden, Roger L.,Schulte-Elte, Karl H.
, p. 2193 - 2202 (1981)
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.
