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- W1986777973 abstract "Abstract Pummerer-derived substituted vinylthionium ions (alyl phenyl sulfoxide, TMSOTf, EtN(i-Pr) 2 , CH 2 Cl 2 , −78°C) with a β-trimethylsilylmethyl ( 2 ), γ-phenyl ( 14 ), or γ-phenyltio ( 15 ) group allylate the enol silyl ethers of acetophenone ( 3 ) and cyclohexanone ( 4 ) in good yield. Allylation with ( 14 ) and ( 15 ) required slow addition of base in order to limit the rate of production of intermediate, and thus avoid unwanted sila-Pummerer type products. Hunigs's base conjugate addition was not observed in these cases. Both the (E)- and (Z)- fors of allyl sulfoxide ( 15 ) were shown to equilibate to the (E)- transoid conformer prior to allylation resulting in exclusive (E)-vinyl sulfide formation. Blocking of the γ-position resulted in preferential α-attack." @default.
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- W1986777973 date "1994-01-01" @default.
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- W1986777973 title "Allylation with Pummerer-generated substituted vinylthionium ions" @default.
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- W1986777973 doi "https://doi.org/10.1016/s0040-4020(01)85513-7" @default.
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