Original scientific paper

Ferrocene Compounds. XXVIII. Synthesis of 2-(Ferrocenylalkyl)- and 2-[Ferrocenyl(phenyl)alkyl]-1,3-propanediols and Their Acetates

Jasmina Lapić ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia
Vladimir Rapić ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia

Abstract

Reaction of the appropriate reagent Fc(CH₂)_nCHRX (1-3, 6, and 9) with sodium salt of diethyl malonate in dry xylene gave 81-91% of the corresponding diethyl (ferrocenylalkyl)malonate or diethyl ferrocenyl(phenyl)alkylmalonate (11). Using Fc(CH₂)_nCHRX (4, 7, 8 and 10) under similar reaction conditions, transesterification products - ethyl ferrocenylalkyl malonates or ethyl ferrocenyl(phenyl)-alkyl malonates (12) were obtained. Reduction of condensation Products 11 with lithium aluminium hydride in diethyl ether gave the corresponding diols 13 (45-66%), which will be in further studies subjected to lipase-mediated transformations with vinyl acetate to chiral monoacetates. By the action of acetic anhydride on diols 13 in a benzene solution, the corresponding mono- 14 (25-52%) and diacetates 15 (36-51%) were obtained.

Keywords

ferrocene compounds; diethyl (ferrocenylalkyl)malonates; ethyl ferrocenylalkyl malonates; 2-ferrocenylalkyl-1,3-propanediols and their acetates

Hrčak ID:

132015

URI

https://hrcak.srce.hr/132015

Publication date:

4.9.2000.

Visits: 1.274 *