Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis( 4-hydroxybenzoyl) ferrocene

Abstract

Abstract Improved methods of synthesis are reported for FcCOC 6 H 4 F-4 1a , FcCOC 6 H 4 OMe-4 1b and Fcd(COC 6 H 4 OMe-4) 2 2b [Fc = (C 5 H 5 )Fe(C 5 H 4 ); Fcd = (C 5 H 4 )Fe(C 5 H 4 )]: demethylation of 1b and 2b , using AlCl 3 in 1,1,2-trichloroethane, yields FcCOC 6 H 4 OH 1f and Fcd(COC 6 H 4 OH) 2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c , hydrazinolysis of which yields FcCOC 6 H 4 NH 2 -4 1d . Crystal structures are reported for 1d, 1f and 2f : in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.