- Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition
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Highly accelerated inverse-electron-demand strain-promoted alkyne-nitrone cycloaddition (IED SPANC) between a stable cyclooctyne (bicyclo[6.1.0]nonyne (BCN)) and nitrones delocalized into a Cα-pyridinium functionality is reported, with the most
- Gunawardene, Praveen N.,Luo, Wilson,Polgar, Alexander M.,Corrigan, John F.,Workentin, Mark S.
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supporting information
p. 5547 - 5551
(2019/08/01)
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- Golden Opportunity: A Clickable Azide-Functionalized [Au25(SR)18]- Nanocluster Platform for Interfacial Surface Modifications
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Ultrasmall atomically precise monolayer-protected gold thiolate nanoclusters are an intensely researched nanomaterial framework, but there is a lack of a system that can be directly synthesized and undergo interfacial surface chemistry. We report an [Au25(SCH2CH2-p-C6H4-N3)18]- nanocluster platform with azide moieties appended onto each surface ligand. The structure of this surface reactive cluster has been confirmed by single-crystal X-ray crystallography, mass spectrometry and ultraviolet visible, infrared and nuclear magnetic resonance spectroscopies. We show that all surface azide moieties are amenable to cluster-surface strain-promoted alkyne-azide cycloaddition chemistry with a strained cyclooctyne, opening this as a new platform to allow functional, postassembly surface modifications to this very prominent nanocluster.
- Gunawardene, Praveen N.,Corrigan, John F.,Workentin, Mark S.
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supporting information
p. 11781 - 11785
(2019/08/22)
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- Efficient Utilization of Tetrabutylammonium Bifluoride in Halofluorination Reactions
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The halofluorination reaction of a variety of alkenes by using tetrabutylammonium bifluoride (TBABF) in the presence of N-halosuccinimide is described.This process occurs stereospecifically to afford anti addition products, and with unsymmetrical olefins a marked Markovnikov-type regioselectivity is observed.In some cases, formation of a remarkable amount of the corresponding dihalo derivatives was found, but this undesirable side reaction can be avoided by using N-iodosucciniumide (NIS) as halogenating agent.If N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) is utilized, these dihalo compounds can be easily removed from the halofluorinated compounds by simple column chromatography on silica gel.A mechanism for this side reaction is postulated.
- Camps, F.,Chamorro, E.,Gasol, V.,Guerrero, A.
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p. 4294 - 4298
(2007/10/02)
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- Photolysis of Some 1-Substituted Cycloocta-1,5-dienes: Synthesis of 1-Fluorotricyclo2,6>octane
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A study of the photolytic behaviour of several derivatives of cycloocta-1,5-diene as possible precursors of bridgehead-substituted tricyclo2,6>octanes is described.Of the substrates examined, only 1-fluorocycloocta-1,5-diene succesfully underwent photocyclization giving 1-fluorotricyclo2,6>octane. 1-Bromocycloocta-1,5-diene suffered fission of the carbon-bromine bond, while cycloocta-1,5-diene-1-carbonitrile afforded a mixture of at least four unsaturated isomers.
- Cotsaris, Evangelo,Della, Ernest W.
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p. 2561 - 2564
(2007/10/02)
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