engleski

Ferrocene compounds XXIII. Synthesis and reactions of the new type of methyl ferrocyloxyalkanoates

The new type of ferrocenyloxaaliphatic acid esters, FcCHROCHR"COOMe (R = H, Me, Ph ; R" = H, Me) (7) has been prepared by the action of alkoxides derived from methyl glycolate or methyl lactate on the corresponding ferrocenylcarbinyl acetates (2) or N, N, N-trimethylferrocylammonium iodides (4). The esters obtained were accompanied by a small quantity of oligomeric esters, FcCHR(OCHR"CO)nOMe (9), and with more or less ferrocyl methyl ethers (8). As opposed to the alkaline hydrolysis of the analogous methyl benzoxyacetate (6) into benzoxyacetic acid (5) the acidification of sodium alkanoates 10 obtained by saponification of esters 7 gave unexpectedly the corresponding ferrocenylcarbinols 1. In a similar way the esters 7 were converted into mixtures of the mentioned carbinols and diferocyl ethers 11 under action of aqueous hydrochloric acid. The mechanisms of the reactions 10 to 1 and 7 to 1, 11 are discussed.

Iron; Ferrocene; Methyl ferrocyloxyalkanoates

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