The synthesis of trigonal bipyramidal, square planar, and octahedral bis(phosphine) complexes of the formula trans-L y M(P((CH 2 ) n CHCH 2 ) 3 ) 2 , and their conversion to gyroscope-like molecules trans-L y via three-fold intramolecular alkene metathesis/hydrogenation sequences, is reviewed. New data involving bis(phosphite) complexes are then described. Reactions of P(NMe 2 ) 3 and HO(CH 2 ) n CHCH 2 (n=a, 3; b, 4; c, 5; d, 6; e, 8; f, 9) afford the ligands P(O(CH 2 ) n CHCH 2 ) 3 (26a–f, 79–96%). Reactions of 26a,b,e,f and Fe(BDA)(CO) 3 (BDA=benzylideneacetone) give trans-Fe(CO) 3 (P(O(CH 2 ) n CHCH 2 ) 3 ) 2 (27a,b,e,f) as yellow or green oils in 17–64% yields after workup. Two representative complexes (27b,e) are treated with Grubbs’ catalyst (2×6.5mol%). NMR analyses of the resulting crude trans-Fe(CO) 3 (P(O(CH 2 ) n CHCH(CH 2 ) n O) 3 P) (28b,e) suggest mixtures of Z/E isomers and perhaps oligomers. Subsequent ClRh(PPh 3 ) 3 -catalyzed hydrogenations afford the title molecules trans (29b,e) as oils of 82–83% purity by 31 P NMR. Although various properties of 29b,e can be compared to 27b,c, they could not be induced to solidify or crystallize, hampering purification.