Spera, M. L.; Harman, W. D. Electrophilic Additions to η2-Thiophene Complexes: Synthesis of Novel Thiophenium and Thiafulvenium Species. Organometallics 1998, 18, 2988.
Publications
1998
. Y. Shen, T.; Harman, D.; Huang, D. F.; Gonzalez, J. Preparation of 7-azabicyclo[2.2.1]heptane and -heptene derivatives as cholinergic receptor ligands, 1998.
Title compds. (I; R1, R4 = H, alkyl, substituted alkyl; R2 = H, alkyl, alkenyl, heterocyclyl, heterocyclylthio, NH2, heterocyclylamino, CONH2, heterocyclylcarbonyl, heterocyclylalkyl, etc.; R3, R5, R6 = H alkyl substituted alkyl, NH2, halo, CO2H, alkoxycarbonyl, alkylsulfonyl, aryl, heteroaryl, arylsulfonyl, etc.; R2R3 may form a cyclic system; R7 = H, alkyl, substituted alkyl, aryl, cycloalkyl) were prepd. to treat disorders assocd. with a decrease or increase in cholinergic activity. Thus, (2-chloro-5-pyridyl)(phenylsulfonyl)acetylene was treated with N-carbomethoxypyrrole to give 7-carbomethoxy-2-(2-chloro-5-pyridyl)-3-(phenylsulfonyl)-7-azabicyclo[2.2.2]-2,5-diene which underwent reductive dephenylsulfonylation with sodium dihydrophosphate and sodium amalgam followed by hydrogenation and decarbomethoxylation to give (±)-epibatidine and endo-epibatidine. (±)-Epibatidine was treated with formamidinate hydrochloride to give N-formamidinylepibatidine dichydrochloride (II). II at 10-7M had 104% inhibition in binding to the acetylcholine nicotinic receptor using a std. binding assay. [on SciFinder(R)]
Orth, S. D.; Barrera, J.; Rowe, S. M.; Helberg, L. E.; Harman, W. D. Reversible β-Hydride Elimination of Amine Ligands Forming Stable cis-η2-Iminium Hydride Os(II) Complexes. Inorg. Chim. Acta 1998, 270, 337.
Kopach, M. E.; Kolis, S. P.; Liu, R.; Robertson, J. W.; Chordia, M. D.; Harman, W. D. Stereodefined Tandem Addition Reactions of η2-Arenes: A Versatile Route to Functionalized Cyclohexenes. J. Am. Chem. Soc. 1998, 120, 6199-6204.
Kolis, S. P.; Chordia, M. D.; Liu, R.; E., K. M.; Harman, W. D. Activation of Styrenes Towards Diels-Alder Cycloadditions by Osmium(II): Synthesis of Stereodefined Decalin Ring Systems. J. Am. Chem. Soc. 1998, 120, 2218.
Kolis, S. P.; E., K. M.; Liu, R.; Harman, W. D. Activation of Benzylic Carbons in η2-Arene Complexes: A Novel and Efficient Synthesis of Functionalized Decalins. J. Am. Chem. Soc. 1998, 120, 6205.
Gunnoe, T. B.; Sabat, M.; Harman, W. D. Reactions of TpRe(CO)2(THF) with Aromatic Molecules. Journal of the American Chemical Society 1998, 120, 8747-8754.
Chordia, M. D.; Harman, W. D. Asymmetric Induction in η2-Arene Complexes of Pentaammineosmium(II). Journal of the American Chemical Society 1998, 120, 5637.
Chen, H.; Liu, R.; Myers, W. H.; Harman, W. D. Dearomatization of Furan: Elementary Transformations of η2-Coordinated Furan Complexes of Pentaammineosmium(II). Journal of the American Chemical Society 1998, 120, 509-520.
Brooks, B. C.; Chin, R. M.; Harman, W. D. The Asymmetric π-bases fac-Re(dien)(PPh3)(PF3)+ and fac-Re(dien)(PPh3)(CO)+: Evidence for Formation of an η2-Furan Complex. Organometallics 1998, 17, 4716-4723.