FERROCENE COMPOUNDS .23. SYNTHESIS AND REACTIONS OF THE NEW-TYPE OF METHYL FERROCYLOXYALKANOATES

The new types of ferrocenyloxaaliphatic acid ester, FcCHROCHR'COOMe (R = H, Me, Ph; R' = H, Me) (7) have been prepared by the action of alko xides derived from methyl glycolate or methyl lactate on the correspon ding ferrocenylcarbinyl acetates (2) or N, N, N-trimethylferrocylammon ium iodides (4). The esters obtained were accompanied by a small quant ity of oligomeric esters, FcCHR(OCHR'CO)(n)OMe (9), and with more or l ess 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 men tioned carbinols and diferrocyl ethers 11 under action of aqueous hydr ochloric acid. The mechanisms of the reactions 10 --> 1 and 7 --> 1, 1 1 are discussed.