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Anionic, in Situ Generation of Formaldehyde: A Very Useful and Versatile Tool in Synthesis

Abstract : A very simple, safe and powerful method for the in situ generation of formaldehyde at low temperature in anhydrous conditions is described. This new tool avoids the use of gaseous formaldehyde and is suitable for basic carbon nucleophiles which cannot be generated in aqueous reaction media. Various substrates, including organolithium reagents and enolates, underwent smooth hydroxymethylation showing the versatility of this process. A Wittig reaction was also carried out in high yield.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385033
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Submitted on : Thursday, November 28, 2019 - 4:06:28 PM
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Geoffrey Deguest, Laurent Bischoff, Corinne Fruit, Francis Marsais. Anionic, in Situ Generation of Formaldehyde: A Very Useful and Versatile Tool in Synthesis. Organic Letters, American Chemical Society, 2007, 9 (6), pp.1165-1167. ⟨10.1021/ol070145b⟩. ⟨hal-02385033⟩

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