Vollhardt, K. Peter - University of California, Berkeley

研究领域

Organic and Organometallic Chemistry — Transition metals and novel synthetic methodology enable the synthesis of complex natural and unnatural products. Professor Vollhardt and his coworkers are interested in the application of transition metals to organic synthesis. The areas under investigation range from the assembly of novel oligometallic arrays to the use of cobalt, palladium, and nickel in the construction of complex organic molecules. For example, his group has developed ways to attach cyclopentadienylmetal units repeatedly to other p-ligands, such as cyclopentadienyl itself. In this way, a number of potentially catalytic and conducting oligocyclopentadienylmetals with remarkable properties have become available for further exploration. A second effort underway is directed at further exploring the scope of the cobalt-mediated [2+2+2]cycloaddition of alkynes to other unsaturated substrates, a reaction pioneered by the Vollhardt group. Recent work has focused on "tagging" heteroaromatic systems, such as the indole alkaloids, resulting in a total synthesis of strychnine and a novel approach to morphinoids. A third problem is concerned with the synthesis of molecules of theoretical importance, in particular highly strained hydrocarbons and molecules with electronically destabilizing features. These include the phenylenes, a class of novel benzenoids in which benzene and cyclobutadiene are fused in an alternating manner. Their properties are remarkable, in particular with respect to cyclohexatrienic reactivity of the benzene nuclei and their potential to behave as organic magnets and conductors.

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Baxter, C. S.; Garratt, P. J.; Vollhardt, K. P. C., The 3,4:5,6:9,10-Tribenzobicyclo[6.2.0]deca-pentaenyl Dianion, J. Am. Chem. Soc. 1969, 91, 7783. Garratt, P. J.; Vollhardt, K. P. C., Benzo[3,4]cyclobuta[1,2-c]thiophen (2-Thianorbiphenylene), Chem. Commun. 1970, 109. Garratt, P. J.; Vollhardt, K. P. C.; Mitchell, R. H., Wittig Reactions of 1,2-Dihydro-1,2-bis(triphenylphosphoranylidene)benzocyclobutene and Benzocyclobutene-1,2-quinone. The Synthesis of Dibenzo[a,c]benzo[3,4]cyclobuta[1,2-f]cyclooctene, J. Chem. Soc. (C) 1970, 2137. Garratt, P. J.; Holmes, A. B.; Sondheimer, F.; Vollhardt, K. P. C., The Synthesis of Benzo[3,4]cyclobuta[1,2-e]dicyclohexeno[b,h]thionin, an Analog of Biphenylene Containing a Thionin Ring, J. Am. Chem. Soc. 1970, 92, 4492. Garratt, P. J.; Vollhardt, K. P. C., 6,11-Methanocyclobutabenzo[1,2-a]-[10]annulene, a Biphenylene-Analog Containing a Carbocyclic 10 π-Electron Ring, Angew. Chem. 1971, 83, 111; Angew. Chem., Int. Ed. Engl. 1971, 10, 125. Garratt, P. J.; Vollhardt, K. P. C., Homophthalaldehyde, Synthesis 1971, 423. Garratt, P. J.; Holmes, A. B.; Sondheimer, F.; Vollhardt, K. P. C., The Synthesis of Mono-trans-dicyclohexeno[b,i]-1,6-dithiacyclodeca-2,4,7,9-tetraene, a Tetra-alkylated 1,6-Dithia[10]annulene, Chem. Commun. 1971, 947. Garratt, P. J.; Vollhardt, K. P. C., Synthesis of Benzo[3,4]cyclobuta[1,2-a]benzo[d]tropylium Cation, a Homobiphenylene Cation, Chem. Commun. 1971, 1143. Garratt, P. J.; Vollhardt, K. P. C., The Synthesis of 6,7-Diphenyl-3-thiabicyclo[3.2.0]heptatriene, a Thienocyclobutadiene, J. Am. Chem. Soc. 1972, 94, 1022. Garratt, P. J.; Vollhardt, K. P. C., Wittig Reactions of 1,2-Benzocyclobutadienequinone. Synthesis of 2-Thianorbiphenylene (Benzo-[3,4]cyclobuta[1,2-c]thiophene), J. Am. Chem. Soc. 1972, 94, 7087. Vollhardt, K. P. C.; Bergman, R. G., 3,6-Dehydrooxepin, a Furocyclobutadiene, J. Am. Chem. Soc. 1972, 94, 8950. Jones, A. J.; Garratt, P. J.; Vollhardt, K. P. C., 13C Shifts in Biphenylene and Analogous Compounds, Angew. Chem. 1973, 85, 260; Angew. Chem., Int. Ed. Engl. 1973, 12, 241. Garratt, P. J.; Vollhardt, K. P. C., Aromatizität; Georg Thieme Verlag: Stuttgart, 1973. Bergman, R. G.; Vollhardt, K. P. C., 3-Oxabicyclo[3,2,0]hepta-1,4-diene, Chem. Commun. 1973, 214. Garratt, P. J.; Holmes, A. B.; Sondheimer, F.; Vollhardt, K. P. C., Wittig Reactions of 1,2-Dihydro-1,2-bis(triphenylphosphoranylidene)benzocyclobutene. Synthesis of All-cis- and Mono-trans-1,2,3,4,6,7,8,9-octahydrodibenzo[b,h]benzo[3,4]cyclobuta-[1,2-e]thionin, Analogues of Biphenylene Containing a Thionin Ring, J. Chem. Soc., Perkin Trans. I 1973, 2253. Vollhardt, K. P. C.; Bergman, R. G., Competition between Sulfur Extrusion and Thermal Synthesis of Thienocyclobutadiene in the Pyrolysis of cis- and trans-1,2-Diethynylthiiranes. Dimerization of the Rearrangement Product to Bisthienocyclooctatetraene, J. Am. Chem. Soc. 1973, 95, 7538. Vollhardt, K. P. C.; Bergman, R. G., A One-Step Synthesis of Benzocyclobutenes Involving Cooligomerization of Linear Mono- and Diacetylenes Catalyzed by η5-Cyclopentadienylcobalt Dicarbonyl, J. Am. Chem. Soc. 1974, 96, 4996. Vollhardt, K. P. C.; Bercaw, J. E.; Bergman, R. G., Isolation of Unstable Bis(η5-cyclopentadienylcobalt) Tricarbonyl from the Irradiation of η5-Cyclopentadienylcobalt Dicarbonyl. Thermal Reactions of this Binuclear Complex Leading to Starting Material and Trinuclear and Tetranuclear Cobalt (I) Complexes, J. Am. Chem. Soc. 1974, 96 4998. Vollhardt, K. P. C., Bis-Wittig Reactions in the Synthesis of Nonbenzenoid Aromatic Ring Systems, Synthesis 1975, 765. Vollhardt, K. P. C., Cyclobutadienoids, Top. Curr. Chem. 1975, 59, 113.