Tetrahedron p. 723 - 726 (1980)
Update date:2022-07-29
Topics:
Burger, J. J.
Chen, T. B. R. A.
Waard, E. R. De
Huisman, H. O.
The isomeric chlorosulfones 3, 4 and 4 are prepared by 1,4-addition of sulfonyl chlorides to isoprene.Dehydrohalogenation affords the corresponding 2- and 3-methylbutadienyl sulfones in a configuration which is dependent on the configuration of the chlorosulfone.Pure Z-2-methylbutadienyl sulfones 1 are obtained by displacement of primary halides by the Z-sulfinate anion 2.The Z-sulfones 1 are isomerized to E/Z-mixtures.The E/Z-mixtures are separated into their components and the configuration of the isomers is established by the NMR-NOE technique.
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