86652-97-3Relevant articles and documents
SYNTHESES A L'AIDE DE SULFONES (XXXVII). SYNTHESE DE TROIS PHEROMONES A UNE DOUBLE LIAISON Z : Z, 8-DDA; Z, 9-DDA; Z, 9-TDA.
Julia, Marc,Stacino, Jean-Pierre
, p. 2469 - 2474 (1986)
The title compounds Z,8-dodecen-1yl acetate, Z,9-dodecen-1yl acetate and Z,9-tetradecen-1yl-acetate have been synthesized in three efficient steps: the reaction mixture from metalated ω-hydroxy sulfones and appropriate aldehydes was quenched with acetic anhydride yielding a diastereoisomeric mixture of β-acetoxy sulfones.Convergent elimination with powdered sodium hydroxide led to the E vinylic sulfone.Stereospecific hydrogenolysis of the sulfonyl group was carried out with sodium dithionite leading to the unsaturated alcohol (> 99percent Z).