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J Org Chem. 2001 Apr 6;66(7):2374-81.

Conformations of allylic fluorides and stereoselectivities of their diels-alder cycloadditions.

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Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.


The preparations of new allylic fluorides from the corresponding alcohols are reported. Conformational analysis is achieved by comparison of experimental NMR measurements with theoretical (B3LYP) calculations of relative energies of conformers and J(H,H) and J(H,F) coupling constants. The Diels-Alder reactions of allylic fluorides are investigated experimentally and theoretically. The stereoselectivities of the reactions were determined by NMR analysis and, in one case, by X-ray crystallography. Theoretical predictions of stereoselectivity based upon transition state modeling provided good agreement with experiment. Theoretical models for allylic fluorides and transition state conformations are reported.

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