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  1. Article ; Online: Enhancing catalytic activity of pyridines

    Richard, Nicholas A / Charlton, Grant D / Dyker, C Adam

    Organic & biomolecular chemistry

    2021  Volume 19, Issue 42, Page(s) 9167–9171

    Abstract: Four pyridines decorated with π-donating iminophosphorano substituents ( ... ...

    Abstract Four pyridines decorated with π-donating iminophosphorano substituents (R
    Language English
    Publishing date 2021-11-03
    Publishing country England
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d1ob01630j
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Bis(Iminophosphorano)-Substituted Pyridinium Ions and their Corresponding Bispyridinylidene Organic Electron Donors.

    Frenette, Brandon L / Arsenault, Nadine / Walker, Sarah L / Decken, Andreas / Dyker, C Adam

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 33, Page(s) 8528–8536

    Abstract: Optimized synthetic procedures for pyridinium ions featuring iminophosphorano (-N= ... ...

    Abstract Optimized synthetic procedures for pyridinium ions featuring iminophosphorano (-N=PR
    Language English
    Publishing date 2021-05-14
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202100318
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Powerful Bispyridinylidene Organic Reducing Agents with Iminophosphorano π-Donor Substituents.

    Hanson, Samuel S / Richard, Nicholas A / Dyker, C Adam

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2015  Volume 21, Issue 22, Page(s) 8052–8055

    Abstract: Four members of a new family of powerful bispyridinylidene organic reducing agents have been prepared, which exploit iminophosphorano (-N=PR3; R = Ph, Cy) π-donor substituents. Electrochemical studies show exceptionally high oxidation potentials, ranging ...

    Abstract Four members of a new family of powerful bispyridinylidene organic reducing agents have been prepared, which exploit iminophosphorano (-N=PR3; R = Ph, Cy) π-donor substituents. Electrochemical studies show exceptionally high oxidation potentials, ranging from 1.30 to 1.51 V versus SCE. These new reductants were shown to effectively convert 1-bromonaphthalene to naphthalene under mild reaction conditions. From the redox potentials, substituent constants (σp(+)) for the iminophosphorano groups Ph3P=N- (-1.82) and Cy3P=N- (-2.21) were determined, demonstrating their superior π-donating properties compared to traditional amino substituents.
    Language English
    Publishing date 2015-05-26
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-x
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.201500809
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Iminophosphorano-Substituted Bispyridinylidenes: Redox Potentials and Substituent Constants from Tolman Electronic Parameters.

    Richard, Nicholas A / Khor, Chun Keat / Hetherington, Sydney M / Mills, Scott L / Decken, Andreas / Dyker, C Adam

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2020  Volume 26, Issue 72, Page(s) 17371–17375

    Abstract: Bispyridinylidenes (BPYs) have emerged as an important class of neutral organic electron donors, with redox potentials that vary widely with choice of substituent. Methods to predict the effect of substitution on the redox potential are therefore highly ... ...

    Abstract Bispyridinylidenes (BPYs) have emerged as an important class of neutral organic electron donors, with redox potentials that vary widely with choice of substituent. Methods to predict the effect of substitution on the redox potential are therefore highly desirable. Here we show that the redox potential of BPYs featuring iminophosphorano substituents (R
    Language English
    Publishing date 2020-11-26
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202004153
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Chemical bonding: Rethinking carbon.

    Dyker, C Adam / Bertrand, Guy

    Nature chemistry

    2009  Volume 1, Issue 4, Page(s) 265–266

    MeSH term(s) Carbon/chemistry ; Ligands ; Metals/chemistry ; Organic Chemicals/chemistry ; Phosphoranes/chemistry
    Chemical Substances Ligands ; Metals ; Organic Chemicals ; Phosphoranes ; Carbon (7440-44-0)
    Language English
    Publishing date 2009-06-14
    Publishing country England
    Document type Comment ; News
    ZDB-ID 2464596-5
    ISSN 1755-4349 ; 1755-4330
    ISSN (online) 1755-4349
    ISSN 1755-4330
    DOI 10.1038/nchem.265
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: A strong organic electron donor incorporating highly π-donating triphenylphosphonium ylidyl substituents.

    Burgoyne, Morgan M / MacDougall, Thomas M / Haines, Zachary N / Conrad, Jordan W / Calhoun, Larry A / Decken, Andreas / Dyker, C Adam

    Organic & biomolecular chemistry

    2019  Volume 17, Issue 45, Page(s) 9726–9733

    Abstract: The π-electron donor strength of a triphenylphosphonium ylidyl group ( ... ...

    Abstract The π-electron donor strength of a triphenylphosphonium ylidyl group (Ph
    Language English
    Publishing date 2019-11-08
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/c9ob01984g
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: catena-phosphorus cations.

    Dyker, C Adam / Burford, Neil

    Chemistry, an Asian journal

    2008  Volume 3, Issue 1, Page(s) 28–36

    Abstract: Recent advances towards a systematic development of catena-phosphorus cations are reviewed. The cations represented in this new and developing chapter in fundamental phosphorus chemistry complement the series of neutral and anionic polyphosphorus ... ...

    Abstract Recent advances towards a systematic development of catena-phosphorus cations are reviewed. The cations represented in this new and developing chapter in fundamental phosphorus chemistry complement the series of neutral and anionic polyphosphorus compounds.
    Language English
    Publishing date 2008-01-04
    Publishing country Germany
    Document type Journal Article
    ISSN 1861-471X
    ISSN (online) 1861-471X
    DOI 10.1002/asia.200700229
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Chemistry. Soluble allotropes of main-group elements.

    Dyker, C Adam / Bertrand, Guy

    Science (New York, N.Y.)

    2008  Volume 321, Issue 5892, Page(s) 1050–1051

    Language English
    Publishing date 2008-08-22
    Publishing country United States
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 128410-1
    ISSN 1095-9203 ; 0036-8075
    ISSN (online) 1095-9203
    ISSN 0036-8075
    DOI 10.1126/science.1162926
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Pushing the limits of neutral organic electron donors: a tetra(iminophosphorano)-substituted bispyridinylidene.

    Hanson, Samuel S / Doni, Eswararao / Traboulsee, Kyle T / Coulthard, Graeme / Murphy, John A / Dyker, C Adam

    Angewandte Chemie (International ed. in English)

    2015  Volume 54, Issue 38, Page(s) 11236–11239

    Abstract: A new ground-state organic electron donor has been prepared that features four strongly π-donating iminophosphorano substituents on a bispyridinylidene skeleton. Cyclic voltammetry reveals a record redox potential of -1.70 V vs. saturated calomel ... ...

    Abstract A new ground-state organic electron donor has been prepared that features four strongly π-donating iminophosphorano substituents on a bispyridinylidene skeleton. Cyclic voltammetry reveals a record redox potential of -1.70 V vs. saturated calomel electrode (SCE) for the couple involving the neutral organic donor and its dication. This highly reducing organic compound can be isolated (44 %) or more conveniently generated in situ by a deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive SN bond cleavage of N,N-dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.
    Language English
    Publishing date 2015-07-24
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201505378
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article: Diverse Reactivity of the cyclo-Diphosphinophosphonium Cation [(PtBu)3Me]+: Parallels with Epoxides and New catena-Phosphorus Frameworks

    Robertson, Alasdair P. M / Burford Neil / Decken Andreas / Dyker C. Adam / Gray Paul A / Patrick Brian O

    Journal of the American Chemical Society. 2014 Oct. 22, v. 136, no. 42

    2014  

    Abstract: The cyclo-diphosphinophosphonium salt [(PtBu)₃Me][OTf] (2) has been shown to be highly reactive toward Lewis bases, exhibiting diverse reactivity with phosphines, 4-(dimethylamino)pyridine (dmap) and chlorophosphines, providing approaches to new open- ... ...

    Abstract The cyclo-diphosphinophosphonium salt [(PtBu)₃Me][OTf] (2) has been shown to be highly reactive toward Lewis bases, exhibiting diverse reactivity with phosphines, 4-(dimethylamino)pyridine (dmap) and chlorophosphines, providing approaches to new open-chain and cyclic catena-phosphorus frameworks. Reaction of 2 with R₃P (R = Me or nPr) or dmap led to the ring-opened adducts [R₃P–PtBu–PtBu–P(Me)tBu][OTf] (R = Me (4a), nPr (4b)) and [(dmap)-PtBu–PtBu–P(Me)tBu][OTf] (6), respectively. The complicated ³¹P{¹H} NMR spectra of the three compounds were simulated, evidencing the presence of two diastereomeric forms of 4a, and single diastereomers of 4b and 6. This ring-opening reactivity of the cation in 2 parallels the reactivity of isolobal epoxides with nucleophiles under acidic conditions. Compound 2 was also shown to react with a 2:1 mixture of Me₂PCl and TMSOTf to form the unexpected cyclo-diphosphino-1,2-diphosphonium salt [(Me₂P)₂(PtBu)₂][OTf]₂ (8), which is postulated to result from two consecutive ring-opening and ring-closing steps. In contrast, reaction with MePCl₂ furnished [(MeP)(PtBu)₂(P(Me)tBu)][OTf] (9), consistent with insertion of a “MeP” moiety into the cationic phosphorus framework of 2. The importance of ring strain on the reactivity of the cation in 2 was illustrated by comparative studies of the corresponding cyclo-tetraphosphorus cation in [(PtBu)₄Me][OTf] (10), which exhibits no reactivity under analogous conditions.
    Keywords cations ; epoxides ; nuclear magnetic resonance spectroscopy ; phosphorus ; pyridines ; stable isotopes
    Language English
    Dates of publication 2014-1022
    Size p. 14941-14950.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021%2Fja507741s
    Database NAL-Catalogue (AGRICOLA)

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