Synthesis of 1, 4-Diketones from Acylcarbonylferrates and Methyl Vinyl Ketone

Abstract

The reactions of acylcarbonylferrates with methyl vinyl ketone were investigated and found to result in the formation of 1, 4-diketones in good yields under mild reaction conditions, R-Br K2Fe(CO)4→K+[RCOFe(CO)3L]- CH2=CHCOCH3 →R-COCH2CH2COCH3The reactions were variously affected accodrding to the solvents used. Dipolar aprotic solvents such as N, N-dimethylacetamide promoted the reactions but in tetrahydrofuran, they did not proceed.Using the present method, important perfume substances such as cis-jasmone and dihydrojasmone could be prepared in good over-all yield in one pot.