Anionic, in situ generation of formaldehyde: a very useful and versatile tool in synthesis.
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. [reaction: see text]
Deguest
Geoffrey
G
Laboratoire de Chimie Organique Fine et Hétérocyclique, CNRS UMR 6014, IRCOF-INSA Rouen, B.P. 08, 76131 Mont-Saint-Aignan, France.
Bischoff
Laurent
L
Fruit
Corinne
C
Marsais
Francis
F