Preparation of 1,3-Diketones and of Nitro-diketones by (1:1)-Acylation of Lithium Enolates with Acyl Chlorides

Article abstract of DOI:10.1002/hlca.19810640313

Slow addition of precooled solutions of lithium enolates in THF to solutions of equimolar amounts of acyl chlorides in the same solvent at temperatures between -80 and -100 deg furnishes 1,3-diketones in acceptable to good yields.Even 3-nitropropionyl and 4-nitrobutyryl chloride can be employed for the (1:1)-acylation of enolates to give the synthetically useful 5- and 6-nitro-1,3-diketones 13 and 25, respectively.The scope and the limitations of this method of preparing 1,3-diketones are given and are compared with alternative methods.