Journal of Organic Chemistry 2012-12-07

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, Adrian L Schwan

Index: J. Org. Chem. 77(23) , 10978-84, (2012)

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Abstract

Dibromotetrachloroethane (C(2)Br(2)Cl(4)) is demonstrated as a 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 CCl(4), CBr(2)F(2) and C(2)Br(2)F(4). A formal synthesis of E-resveratrol is demonstrated using C(2)Br(2)Cl(4).