Journal of Organic Chemistry p. 3170 - 3174 (1985)
Update date:2022-08-11
Topics:
Engman, Lars
Bystroem, Styrbjoern E.
Sodium 2-thienyltellurolate, generated in catalytic amounts from sodium borohydride and bis(2-thienyl) ditelluride, was found to efficiently debrominate 1,4-dibromo-2-olefins to 1,3-dienes under very mild reaction conditions.The required 1,4-dibromo-2-olefins were usually synthesized by allylic α,α'-bromination of olefins.Terminal olefins yielded, via allylic rearrangement, a mixture of 1,4-dibromo-2-olefins and 1,2-dibromo-3-olefins.Both these isomers were converted to 1,3-dienes (E/Z ca. 9/1) by the tellurolate reagent.The syntetic utility of the tellurolate-induced debromination reaction was demonstrated in a two-step synthesis of the main component of the red bollworm moth sex pheromone.
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