[2,3]-Wittig rearrangement by a chlorine-lithium exchange |
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Authors: | Beatriz Maciá |
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Institution: | Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain |
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Abstract: | The reaction of different allylic chloromethyl ethers 1 with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (2.5 mol %) in THF at 0 °C for 1 h gives, after hydrolysis with water, the expected alcohols 2 resulting from a 2,3]-Wittig rearrangement, in an exclusive manner. The same process can also be applied to the corresponding 1,2]-Wittig rearrangement, as it is exemplified for benzyl chloromethyl ether. |
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Keywords: | [2 3]-Wittig rearrangement DTBB-catalysed lithiation Chlorine-lithium exchange Allylic chloromethyl ethers |
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