Acid catalysed condensation reactions of 1,3-dihydroxybenzene with new redox-active metallocene aldehydes

Beer PD, Drew MGB, Hesek D, Lacy SM

New ferrocene and cobaltocenium acetal and aldehyde containing compounds have been prepared. The acid catalysed condensations of both metallocene bis(aldehydes) (5, 6) with 1,3-dihydroxybenzene yielded complex products. The new metallocene cyclic monoaldehydes (7, 8), differed markedly in their reactions with 1,3-dihydroxybenzene with the ferrocene derivative 8 producing [1 + 1] and [1 + 2] bisphenol: aldehyde adducts, whereas the cobaltocenium analogue gave a cyclic diene compound (16). A single crystal X-ray structure of 16 is also described and the electrochemical properties of some of the new metallocene derivatives reported.