Deprotonation of the propargyl site of racemic or enantiomerically pure Tp'(CO)IW(C6H5C=CCH3) (Tp'= hydridotris(3,5-dimethylpyrazolyl)borate yields an eta(2)-allenyl anion which has been reacted with a series of aldehydes and ketones possessing electron-donating substituents. Elimination under either acidic or basic conditions generates chiral trans conjugated enynes. Characterization has been accomplished by NMR, IR, UV-vis, and elemental analysis. Additionally, X-ray diffraction has been used to structurally characterize racemic Tp'(CO)IW(C6H5C=CCH=C(CH3)C5H4FeC5H5) The structural analysis reveals a centrosymmetric space group (<P(1)over bar>); cell dimensions of a = 10.690(5) Angstrom, b = 13.360(7) Angstrom, c = 15.392(7) Angstrom, alpha = 92.57(6)degrees, beta = 101.70(5)degrees, and gamma = 100.97(4)degrees; Z = 2 molecules/unit cell; and R(w) = 4.7% and R = 3.9%. Second harmonic generation of the enynes has been measured by the Kurtz powder technique.