Carbon tetrahedron

WH Daly, D Poche. The preparation of V-carboxyanhydridcs of a-amino acids using bis(trichloromethyl)carbonate. Tetrahedron Lett 29, 5894, 1988. 

Rocke suggests that, like the atomic theory, the benzene theory was both extremely popularbecause it was successfulawd disbelieved in realist terms. 52 In both cases, and in the case of the carbon tetrahedron, there were two compelling problems that deterred most chemists from believing they had a real, probably true theory. 

But what about the three-dimensional images or formulations of molecules What about "la chimie en l espace" introduced by Joseph Achille Le Bel, van t Hoff, and Wislicenus toward the end of the nineteenth century Were these carbon tetrahedra realistic "models" of real molecules in space Van t Hoff argued in favor of the carbon tetrahedron that if atoms were arranged in a plane, there would be more isomers of the type CR1R2R3R4 predicted in principle than are actually observed. With the tetrahedral structure, only two isomers are possible, related to each other as mirror images. 102... 

In the 1930s, the French chemist Georges Urbain argued that the carbon tetrahedron is a valuable mental construct but that it cannot be a "model," because in physical science a model must take mechanism and force into account. The representation of the double bond by one of the sides of a double tetrahedron is a pure symbol. 

It was precisely a dynamic view of the molecule, replacing the static concept of the carbon tetrahedron, that was taken by Lapworth and Lowry, as they worked in Armstrong s laboratory in the 1890s and early 1900s. 

But it was not really until 1931, when Slater and Pauling independently developed methods to explain directed chemical valence by orbital orientation that it can truly be said that a chemical quantum mechanics, rather than an application of quantum mechanics to chemistry, had been created. In a study of Slater, S. S. Schweber notes the distinction between the Heitler-London-Pauling-Slater theory and the Heitler-London theory. Heitler and London successfully explained the electron-valence pair on the basis of the Goudsmit-Uhlenbeck theory of spin. Slater and Pauling explained the carbon tetrahedron. This second explanation distinguishes quantum chemistry from quantum physics.2... 

Shieh, W. and Dell, S. and Repic, 0. (2002). Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate. Tetrahedron Letters, 43, 5607-5609. 

A spatial or three-dimensional formula for nitrogen, analogous to the carbon tetrahedron, is not possible because there is no symmetrical solid figure with five corners. Hence it was assumed that certain valencies of the nitrogen atom are directed in special directions. Thus were obtained J. H. van t Hoff s cubic or tetrahedral formula, C. Willgerodt s double tetrahedron, C. A. Bischoff s square pyramid, and the modifications suggested by W. Vaubel, and A. von Baeyer. The tetrahedral and the pyramidal or square formula can be graphically symbolized . ... 

For tetralithiotetrahedrane, (CLi)4, the structure with the lithium atoms above the faces of the carbon tetrahedron was found in the calculations to be more stable than with the lithium atoms above the vertices (Figure 3-27) [73],... 

Gung, B. W. Diastereofacial selection in nucleophilic additions to unsymmetrically substituted trigonal carbons, Tetrahedron 1996, 52, 5263-5301. 

His, S., Meyer, C., Cossy, J., Emeric, G., Greiner, A. Solid phase synthesis of amides by the Beckmann rearrangement of ketoxime carbonates. Tetrahedron Lett. 2003, 44, 8581-8584. 

Andrews, G., Evans, D. A. Stereochemistry of the rearrangement of allylic sulfonium ylides. New method for the stereoselective formation of asymmetry at quaternary carbon. Tetrahedron Lett. 1972, 5121-5124. 

Shimizu, i., Minami, i., Tsuji, J. Paiiadium-cataiyzed synthesis of a, 3-unsaturated ketones from ketones via aiiyi enoi carbonates. Tetrahedron Lett. 1983, 24,1797-1800. 

Yamauchi, Y., Kawate, T., Katagiri, T. and Uneyama, K. (2003) Generation and reactions of a-trifluoromethyl stabilized aziridinyl anion, a general synthetic precursor for stereospecific construction of a-amino-a-trifluoromethylated quaternary carbon. Tetrahedron Lett., 44, 6319-6322. 

Coutrot, P., Grison, C., and Charbonnier-Gerardin, C., Synthesis of modified peptides incorporating a phosphorane moiety in a terminal nitrogen or carbon, Tetrahedron, 48, 9841, 1992. 

Casadei MA, Inesi A, Rossi L (1997) Electrochemictil activation of caibon dioxide synthesis of oiganic carbonates. Tetrahedron Lett 38 3565-3568... 

Casadei MA, Cesa S, Feroci M, Inesi A (1997) The O VCO system as mild tmd safe carboxy-lating reagent synthesis of oiganic carbonates. Tetrahedron 53 167-176... 

Hasegawa, M. Ishii, H. Fuchigami, T. Electroorganic synthesis under solvent-free conditions. Highly regioselective anodic monofluorination of cyclic ethers, lactones, and a cyclic carbonate. Tetrahedron Lett. 2002, 43, 1503-1505. 

Baran, A., Kazaz, C., Se9en, H., Sutbeyaz, Y. 2003. Synthesis of haloconduiitols from an endo-cycload-duct of furan and vinylene carbonate. Tetrahedron 59 3643-3648. 

Tsuji J, Minami I, Shimizu I. Palladium-catalyzed allylation of ketones and aldehydes via allyl enol carbonates. Tetrahedron Lett. 1983 24 1793-1796. 

Kang S, Park D, Jeon J, Rho H, Yu C. Highly regioselective palladium-mediated substitution of allylic and dienylic cyclic carbonates. Tetrahedron Lett. 1994 35 2357-2360. 

Fisher, C., and H. S. Mosher Asymmetric Homogenous Hydrogenation with Phosphine-Rhodium-Complexes Chiral Both at Phosphorus and Carbon. Tetrahedron Letters 1977,2487. 

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