Organic cage compounds

The hollow interior of dodecahedrane and other organic cage compounds described in section 4.9 is much too small to envelop atoms, ions, or molecules. Tight closed-shell macromolecules have been obtained from vesicles by several research groups, by polymerization of amphiphiles possessing double or triple bonds within the membrane or at the head groups. Smaller, but well-defined, closed-shell containers have been obtained by two other methods described below, namely by directed synthesis and by formation of closed-shell all-carbon molecules in graphite vapor. 

Organic cage compounds formed by covalent bonds alone have been synthesized with the help of dynamic covalent bond formation. Cage compounds through formation of imine bonds (hemicarcerands, cavitands, adamantoid nano-cages and chiral nano-cubes based on chiral... 

Mastalerz M (2010) Shape-persistent organic cage compounds by dynamic covalent bond formation. Angew Chem Int Ed 49 5042-5053... 

Schneider MW, Lechner LG, Mastalerz M (2012) Uniform porous nanospheres of discrete shape-persistent organic cage compounds. J Mater Chem 22(15) 7113-7116... 

Post-modification of the interior of porous shape-persistent organic cage compounds. Angew Chem Int Ed 52(13) 3611-3615... 

Brutschy M, Schneider MW, Mastalerz M, Waldvogel SR (2013) Direct gravimetric sensing of GBL by a molecular recognition process in organic cage compounds. Chem Commun 49(75) 8398-8400... 

Zhang G, Mastalerz M (2014) Organic cage compounds — from shape-persistency to function. Chem Soc Rev 43(6) 1934-1947... 

Quaternary onium salts were the first phase-transfer catalysts used subsequently, a number of compounds (linear polyethers, polypodands, crown-ethers, cryptands, cage-compounds, etc.) were found effective for the anion activation in two-phase systems. These structurally different systems must satisfy at least two fundamental conditions in order to behave as phase-transfer catalysts i) solubility in the organic phase ii) steric hindrance around the cationic center leading to a good cation-anion separation within the ion-pair. 

Little is known about the reactions of radical cations of organophosphorus compounds (P such as aryl phosphates and phosphonates as caged compounds and reagents in organic syntheses [85-91]. To elucidate PET reactions including P as the key intermediate, PR and -y-R are used here. 

Kroto, H. W. Walton, D. R. M. 1992 Postfullerene organic chemistry. In Carbocyclic cage compounds (ed. E. Osawa O. Yonimitsu). London and New York VCH Publishers. 

Desferrioxamine E and its analogues are siderophores widely produced by Streptomyces and related bacteria.81 Their major role is ferric transportation cells secrete these cage compounds to their environment and then uptake their ferric-bound form (ferrioxamines) by the activity of a specific transporter to utilize ferric. Probably, the organisms had developed this complex retrieval system due to the insolubility and low availability of ferric in the natural environment. 

Figure 11 CD and UV spectra of (6R,15R)-(+)-6,15-dihydro-6,15-ethanonaphtho[2,3-c]pentaphene 3 in dioxane/EtOH and chemical correlation between compound 3 and related compounds, where the most ideal chiral cage compound 3 with two anthracene chromophores shows intense exciton-coupled CD Cotton effects, establishing the consistency between X-ray Bijvoet and CD exciton chirality methods. Redrawn from N. Harada K. Nakanishi, Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books Mill Valley, CA, and Oxford University Press Oxford, 1983.

Highly strained cage compounds have long attracted considerable attention from both experimentalists and theoreticians.724 The most important structural component of cage compounds is very often a highly strained cyclobutane ring, which is easily accessible by a photochemical route.725 Cubane for its aesthetic beauty counts as one of the milestones in synthetic (photo)chemistry and structural organic chemistry.726 A... 

Gleiter, R., Treptow, B., Photochemical Synthesis of Cage Compounds Propellaprismanes and Their Precursors. In Horspool, W. M., Song, P. S. (eds), CRC Handbook of Organic Photochemistry and Photobiology, CRC Press, Boca Raton, FL, 1995, pp. 64 83. 

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