1,2-Dibromotetrachloroethane: An Ozone-Friendly Reagent for the in Situ Ramberg-Bäcklund Rearrangement and Its Use in the Formal Synthesis of E-Resveratrol

Stefan C. Söderman and Adrian L. Schwan*

*Department of Chemistry, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Email: schwanuoguelph.ca

S. C. Söderman, A. L. Schwan, J. Org. Chem., 2012, 77, 10978-10984.

DOI: 10.1021/jo3021852

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Abstract

Solid 1,2-dibromotetrachloroethane (C₂Br₂Cl₄) is a suitable halogenating reagent for the one-pot conversion of sulfones to alkenes by way of the Ramberg-Bäcklund rearrangement. Dibromotetrachloroethane successfully replaces known ozone depleting agents CCl₄, CBr₂F₂ and C₂Br₂F₄. A formal synthesis of E-resveratrol is demonstrated.

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Key Words

Ramberg-Bäcklund Reaction, Green Chemistry

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ID: J42-Y2012-3800