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Fragmentation of Homoallylic Alkoxides. Thermolysis of potassium 2-substituted bicyclo [2.2.2]oct-5-en-2-alkoxides (1981)

Snowden, Roger L. ; Schulte-Elte, Karl H.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 64 (1981), S. 2193-2202

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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

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