ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Thermolysis of the potassium 2-substituted bicyclo [2.2.2]oct-5-en-2-alkoxides derived from alcohols 2-17 at 90-120° 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640726