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Guide Molecular Encapsulation: Organic Reactions in Constrained Systems

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DFT calculations have been performed to study the course of dichlorocarbene insertion reactions into alkanes and to better understand the regio- and stereoselectivities observed. The reactivity of a specific C-H bond is determined by the capacity of the remaining alkyl fragment to effectively delocalize the partial positive charge buildup during the reaction.

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This activity can readily be estimated by calculation of the hydride transfer potential HTP. A comparison with the structure and the stability of the corresponding cation is useful to emphasize the origins of the selectivity. Dichlorocarbene is also predicted to react efficiently with acidic C-H bonds through a nucleophilic-electrophilic mechanism. In principle, an attack of a carbene on an appropriately substituted three-membered ring may lead to fragmentation of the molecule. Mechanisms and Regio- and Stereoselectivities Udo H.

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Novel insertion reactions of dichloro- and dibromocarbene into carbon-hydrogen bonds adjacent to cyclopropane rings are reported. It is found that the predominant isomers formed in the reactions with bicyclo[4. In the reactions of bicyclo[3. In some compounds cyclopropane rings "activate" adjacent carbon-hydrogen bonds, whereas other systems containing three-membered rings do not.

Moreover, the influence of various substituents methyl, geminal dimethyl, phenyl, methoxy, and ethoxy attached to bicyclo[3. In stark contrast, selective insertion into the tertiary carbon-hydrogen bonds of the cyclobutane ring in bicyclo[4. Jean-Luc Mieusset, Udo H. The bicyclic alkenylidenes 9 bicyclo[3. Moreover, they show that these carbenes are very reactive and rearrange rapidly, mainly through a 1,2-vinyl shift by overcoming a low barrier 1. In 17 and bicyclo[4. Brinker Organic Letters , 9, The results suggest that among the alkenylidenes investigated in this study, only those with a norbornenylidene structure represent strongly stabilized carbenes with a reduced reactivity toward intermolecular reactions.

Further stabilization is found when the double bond is electron-rich or pyramidalized. Wolfgang Felzmann, Vladimir B. Inclusion of achiral carbene precursor endo azibicyclo[3. The combined methods of induced circular dichroism, NMR spectroscopy, and X-ray structure determination were employed for the first time for structural elucidation of the complexes in solution and the solid state. Significantly different orientations of 1 were observed. The inclusion of small guest molecules within suitable host compounds results in constrained systems that imbue novel properties upon the incarcerated organic substrates.

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Supramolecular tactics are becoming widely employed and this treatise spotlights them. Often, the impact of encapsulation on product formation is substantial. The use of constrained systems offers the means to steer reactions along desired pathways. A broad overview of various supramolecular approaches aimed to manipulate chemical reactions are featured. A reinvestigation of the thermolysis of 4,4-dibromotetracyclo[6.

DFT calculations show that the novel tandem retro-Diels-Alder-Diels-Alder reaction with role reversal is slightly less favored than the overall single-step Cope rearrangement. Brinker Journal of the American Chemical Society , , A fully substrate controlled stereoselective route to construct cis -hexahydronaphthalene 4 is described starting from nonracemic butenolide 6. The key step is an exo -selective transannular Diels-Alder reaction TADA of tetraene 5 , whose intrinsic constraint allows selective formation of one stereodefined product.

Compound 4 is a key intermediate in the synthesis of the novel antibiotic branimycin 1.


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Reactions of endo Diazotricyclo[3. Brinker Journal of Organic Chemistry , 71, Our purpose is to alter the reactivity of a carbene and enhance the regioselectivity of its reactions. By complexation of the carbene precursor, the reactive species is confined in a restricted space and is severely limited to react indiscriminately. Other links View at http: Set up My libraries How do I set up "My libraries"?

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Public Private login e. Add a tag Cancel Be the first to add a tag for this edition. The inclusion of small visitor molecules inside appropriate host compounds leads to restricted structures that imbue novel houses upon the incarcerated natural substrates. Supramolecular strategies have gotten generally hired and this treatise spotlights them.

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A extensive evaluate of assorted supramolecular techniques aimed to govern chemical reactions are featured. The following subject matters are lined in detail:. Read Online or Download Molecular Encapsulation: Advances in Carbohydrate Chemistry, Vol.


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