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[1,2]-Wittig rearrangement from chloromethyl ethers
Gómez, Cecilia,Maciá, Beatriz,Lillo, Victor J.,Yus, Miguel
, p. 9832 - 9839 (2007/10/03)
The reaction of different chloromethyl ethers 1 with an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (2.5 mol %) in THF at 0 °C leads to the corresponding α-lithiomethyl ether intermediates, through a chlorine-lithium exchange, which spontaneously undergo a clean [1,2]-Wittig rearrangement affording the expected homobenzylic alcohols 2. This is the first version of this rearrangement starting from easily available chloromethyl ethers.
