Tetrahedron Letters p. 5791 - 5794 (1985)
Update date:2022-08-03
Topics:
Ishibashi, Hiroyuki
Komatsu, Hajime
Maruyama, Kazumi
Ikeda, Masazumi
A Pummerer rearrangement product, 4-chlorophenylthiomethyl trifluoroacetate (6), obtained from 4-chlorophenyl methyl sulfoxide (5) and trifluoroacetic anhydride, reacted with 1-alkenes in trifluoroacetic acid to give the ene products 8, which were readily converted into terminal 1,3-dienes 10 by oxidation and subsequent pyrolysis.Using this method, 9,11-dodecadien-1-yl acetate (12), a sex pheromone of the red bollworm moth, was synthesized.
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