(E)- AND (Z)-1-BENZENESULFONYL-4-TRIMETHYLSILYL-2-BUTENES AS (E)-1-(1,3-BUTADIENYL) SYNTHONS

Article abstract of DOI:10.1016/S0040-4039(01)80117-9

(E)- and (Z)-1-benzenesulfonyl-4-trimethylsilyl-2-butenes (E/Z=9), prepared from 4-trimethylsilyl-1-buten-3-ol, n-butyllithium and benzenesulfenyl chloride and oxidation of the intermediate (E)- and (Z)-1-benzenesulfinyl-4-trimethylsilyl-2-butenes with hydrogen peroxide, react with n-butyllithium and then primary halides to give 4-benzenesulfonyl-1-trimethylsilyl-2-alkenes which are rapidly 1,4-debenzenesulfonyltrimethylsilated to (E)-1,3-alkadienes by tetra-n-butylammonium fluoride at 0 deg C.