ALKOXIDE-ACCELERATED SIGMATROPIC SHIFTS OF BICYCLONON-6-EN-2-OLS. SUBSTITUENT EFFECTS AND TANDEM - SIGMATROPIC REARRANGEMENTS

Article abstract of DOI:10.1246/cl.1984.1879

Bicyclo<3.2.2>non-6-en-2-ols are shown to undergo <1,3> sigmatropic shifts under the influence of KH and 18-crown-6.A series of the 2-endo-vinyl alcohols were transformed into the ring-expanded ketones, bicyclo<5.2.2>undec-8-en-4-ones, via the tandem <1,3>-<3,3> sigmatropic rearrangements.