Synthetic Approaches to 1,2-Heteraphosphacyclanes

The cover picture shows the mechanism of DNAzyme displacement required to control DNAzyme catalysis for the implementation of programmable molecular logic, as reported by D. Stefanovic, S. W. Graves et al. on . This approach combines the advantages of DNA strand displacement for programming reaction pathways with the inherent catalytic activity of DNAzymes for amplified fluorescent readout. Arbitrary input strand detection was achieved through the rational introduction of mismatched bases. Given the range of chemical reactions catalyzed by DNAzymes, this work offers a powerful mechanism for controlling a range of covalent chemical modifications by using DNA strand displacement. The image was produced with assistance from Kim Miller.

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“…Subtypes 1 and 2 produce uniquely 1,2‐heterophosphacyclanes, a subject that has already been reviewed 8…”

Section: Intramolecular Nucleophilic‐addition‐type Reactionsmentioning

confidence: 99%

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

et al. 2014

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“…Tricoordinate phosphorus compounds are known to undergo a number of addition reactions with unsaturated organic substrates. [1][2][3] For instance, polarized alkenes undergo conjugate addition to give dipolar intermediates I, which are key intermediates in numerous organophosphorus-mediated and -catalyzed transformations. [4][5][6][7][8][9][10][11][12][13][14] For certain α,βunsaturated carbonyl compounds, the intermediate phosphonium enolate can undergo a ring closing to give persistent cyclic σ 5 ,λ 5 -phosphoranes II through a stepwise, formal [4+1] addition.…”

Section: Introductionmentioning

confidence: 99%

Addition reactions of a phosphorus triamide to nitrosoarenes and acylpyridines

Grotenhuis

Mattos

Radosevich

2020

Phosphorus, Sulfur, and Silicon and the Related Elements

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Tricoordinate phosphorus compounds react with a wide variety of double bonds through addition reactions. The dipolar and cyclic products formed are important intermediates in organophosphorus chemistry. We investigated the reactivity between phosphorus triamide 1 and nitrosoarenes and 2-acylpyridines. For sterically congested substrates, the formation of σ 5 , λ 5-phosphorus products is observed. DFT calculations indicate this product is formed through a concerted [4+1] mechanism. For less sterically congested substrates, products are observed arising from cleavage of the N=O or C=O bond with formation of a terminal P=O bond and aryl nitrene or carbene migration into a P-N bond of the phosphorus triamide core. DFT calculations are consistent with an initial [2+1] addition to phosphorus followed by formal carbene/nitrene migration in these cases.

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“…The most common approach to larger phosphaheterocycles is based on a variety of intramolecular cyclizations. Their properties differ greatly depending on the size of the ring and substituents at the phosphorus atom . These compounds have found various applications such as ligands in homogeneous catalysis .…”

Section: Introductionmentioning

confidence: 99%

Ring Enlargement of N-Phosphanyl-1,2,3,4-tetrahydroquinazolines

et al. 2020

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We found that 1-phosphanyl-1,2,3,4-tetrahydroquinazolines undergo ring enlargement. Their treatment with trifluoroacetic or hydrochloric acid afforded diazaphosphepinium salts. Deprotonation of these salts gave the corresponding neutral diazaphosphepines. The reaction of 1-phosphanyl-1,2,3,4-tetrahydroquinazolines with diazomethane or phenylazide afforded triazaphosphocine derivatives via insertion of P–N moiety. At the same time, an analogous hexahydropyrimidine derivative reacted with phenylazide in a normal manner at the phosphorus atom to afford the P(V) derivative.

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Synthetic Approaches to 1,2-Heteraphosphacyclanes

Cited by 6 publications

References 144 publications

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

Addition reactions of a phosphorus triamide to nitrosoarenes and acylpyridines

Ring Enlargement of N-Phosphanyl-1,2,3,4-tetrahydroquinazolines

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