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A synthetic alternative to the type-II intramolecular 4 + 3 cycloaddition reaction
Richard S Grainger1, Richard B Owoare, Patrizia Tisselli
1Department of Chemistry, King's College London, Strand, London WC2R 2LS. richard.grainger@kcl.ac.uk
The Journal of Organic Chemistry
|September 27, 2003
Abstract:
Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.