Synthesis and Characterization of tricarbonyl(trimethylenemethane)iron complexes: crystal structure of (2-methylene-6-p-nitrobenzoyloxy-heptan-1,3-diyl)Fe(CO)3
Transition Metal Chemistry
A series of substituted tricarbonyl(trimethylenemethane)-iron complexes were prepared by functionalization of (3-butenyltrimethylenemethane)Fe(CO)3 (3) or (formyltrimethylenemethane)Fe(CO)3 (14). The products are characterized by 1H and 13C-n.m.r., i.r. and high resolution mass spectroscopy. In addition, the X-ray diffraction analysis of one of these derivatives (13a) was accomplished. Reactions of (3), which introduce a new chiral centre, occur in a non-diastereoselective fashion, while reactions of (14) that introduce a new chiral centre proceed with good diastereoselectivity. The remote nature of the reactive functionality and the (TMM)Fe(CO)3 group is responsible for the lack of diastereoselectivity for (3). The present work demonstrates the robust nature of the (TMM)Fe(CO)3 fragment, embodied in its resistance toward oxidation, and to attack by nucleophiles.