Abstract
Diethyl acetonedicarboxylate (DADC)-magnesium complex, (DADC)2Mg (5b), was isolated from the reaction of DADC and MgCl2 with Et3N, or by the removal of coordination water from (DADC)2Mg·2H2O (5a). Compound 5b could be regarded as an intermediate in the selfcondensation of DADC to give 1, 2, 3, and 4. A mechanism is proposed for the formation of these products from 5b. Acylation of 5a, b was carried out. The reaction of 5b with acyl chloride gave the monoacylated DADC (9) as the main product. The reaction of 5a, b with diketene afforded diethyl homophthalate (4) and orsellinic acid (11) derivatives, formed by acylation and subsequent cyclization.
