ARENE CHROMIUM AND MANGANESE TRICARBONYL ANALOGS OF THE PCP RECEPTOR LIGANDS 5-METHYL-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5,10-IMINE (MK-801) AND 10,5-(IMINOMETHANO)-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTENE (IDDC)

Chromium tricarbonyl complexes of MK-801 (2), IDDC (4), and 3-Cl-IDDC (10) were prepared by arene exchange with benzenechromium tricarbonyl. The resulting complexes retained binding affinity for the PCP receptor, as reflected by IC50 values relative to [H-3]-2. A manganese tricarbonyl analog 28 of 4 was synthesized in which the D ring of 4 was replaced with cyclopentadienylmanganese tricarbonyl. However, 28 showed significantly diminished binding affinity for the PCP receptor, relative to 4. Attempts to prepare a ferrocene analog of 4 in which the A or D rings were replaced with ferrocene failed, due to a very stable carbocation formed in the last step of the synthetic route; the novel alcohols 25 and 29 were formed instead.