NMR Spectroscopy of Cyclobutanes

Seidl, Peter Rudolf; Dias, Jacques F.

doi:10.1002/0470864028.ch6

Cited by 6 publications

(3 citation statements)

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“…Cyclobutane natural products also have proven to be challenging to properly elucidate using standard spectroscopic methods, particularly NMR. 15 Numerous stereochemical and constitutional errors have been made in the literature when attempting to determine the structure of cyclobutane-containing natural products. 16 These misinterpretations likely derive from the fluxional nature of the cyclobutane ring system that rapidly undergoes ring flipping, resulting in unpredictable NMR chemical shifts that have been described as “rather erratic”.…”

Section: Introductionmentioning

confidence: 99%

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Applications of C–H Functionalization Logic to Cyclobutane Synthesis

2014

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The application of C–H functionalization logic to target-oriented synthesis provides an exciting new venue for the development of new and useful strategies in organic chemistry. In this article, C–H functionalization reactions are explored as an alternative approach to access pseudodimeric cyclobutane natural products, such as the dictazole and the piperarborenine families. The use of these strategies in a variety of complex settings highlights the subtle geometric, steric, and electronic effects at play in the auxiliary guided C–H functionalization of cyclobutanes.

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Section: Introductionmentioning

confidence: 99%

“…Cyclobutane natural products also have proven to be challenging to properly elucidate using standard spectroscopic methods, particularly NMR . Numerous stereochemical and constitutional errors have been made in the literature when attempting to determine the structure of cyclobutane-containing natural products .…”

Section: Introductionmentioning

confidence: 99%

Applications of C–H Functionalization Logic to Cyclobutane Synthesis

2014

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“…1 H− 1 H spin−spin coupling between H-6 and H-5 (10−11 Hz) and between H-1 and H-7 (about 5 Hz) supports the assignment of cis orientation of H-5 and H-6 and trans orientation of H-1 and H-7, which corresponds to exo orientation of the C-7 substituent. In a recent review on the NMR spectroscopy of cyclobutanes, limited outdated data on the coupling constants within a four-membered ring show that cis vicinal coupling constants are about 9 Hz, but trans coupling constants may be as low as 4.5 Hz and reach in some cases 10 Hz. This is understandable on the basis of the Karplus equation.…”

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confidence: 99%

A Novel Diastereoselective Multicomponent Cascade Reaction

et al. 2010

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Photocontrolled Binding of Styrylnaphthyridine Ligands to Abasic Site‐Containing DNA by Reversible [2+2] Cycloaddition and Cycloreversion

Schlosser,

Ihmels

2024

Chemistry A European J

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Five novel styrylnaphthyridine derivatives were synthesized and shown to operate as photoswitchable, selective ligands for abasic site‐containing DNA (AP‐DNA), which is an important therapeutic and diagnostic target. These compounds associate with AP‐DNA with binding constants of 0.5–8.4 × 104 M–1 as shown by photometric and fluorimetric titrations. Specifically, these ligands bind preferentially to AP‐DNA relative to regularly paired duplex DNA. As a special feature, the association of these ligands with DNA can be controlled by means of a reversible [2+2] photocycloaddition. Upon irradiation at 420 nm the photodimer is formed, which does not bind to AP‐DNA. In turn, the naphthyridine is regained with excitation at 315 nm. Most notably, this photoinduced deactivation and release of the DNA ligand can be performed in situ in the presence of AP‐DNA, thus providing a tool for on‐demand delivery of a DNA binder. Overall, these results provide a promising starting point for the development of functional AP‐DNA ligands whose bioactivity can be modulated by light with local and temporal control.

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NMR Spectroscopy of Cyclobutanes

Cited by 6 publications

References 0 publications

Applications of C–H Functionalization Logic to Cyclobutane Synthesis

Applications of C–H Functionalization Logic to Cyclobutane Synthesis

A Novel Diastereoselective Multicomponent Cascade Reaction

Photocontrolled Binding of Styrylnaphthyridine Ligands to Abasic Site‐Containing DNA by Reversible [2+2] Cycloaddition and Cycloreversion

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