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Journal articles on the topic 'Diazoalkanes – Reactivity'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Arz, Marius I., David Hoffmann, Gregor Schnakenburg, and Alexander C. Filippou. "NHC-stabilized Silicon(II) Halides: Reactivity Studies with Diazoalkanes and Azides." Zeitschrift für anorganische und allgemeine Chemie 642, no. 22 (October 7, 2016): 1287–94. http://dx.doi.org/10.1002/zaac.201600286.

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2

Schneider, Jörg J. "Reactivity of an Arene Cobalt Triple Decker Complex Towards Various Ligands. Facile Arene Displacement in [Bis{( η5-pentamethylcyclopentadienyl)cobalt}-μ-{η4: η4-toluene}]." Zeitschrift für Naturforschung B 50, no. 7 (July 1, 1995): 1055–60. http://dx.doi.org/10.1515/znb-1995-0712.

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The triple decker complex [{(η5-Cp*)Co}2-μ-{η4: η4-toluene}] 1b exhibits an unusual reactivity towards a variety of organic ligands, 1b reacts with CO, ethene, butadiene, H2, Al2O3, hexafluorobenzene, 1.5 Cod, 2-butyne, phenanthrene, naphthalene and the dinuclear Ni cluster [{(η5-Cp)NiP(C2H5)3}2] to form mainly mononuclear organocobalt complexes. Reaction of 1b with NO and the diazoalkanes di-t-butyl-diazomethane and 2-diazo-1,1′,3,3′-tetramethylcyclohexane results in the formation of the dinuclear complexes [{(η5-Cp*)CoNO}2], [{(η5-Cp*)(di-t-butyl-diazomethane)Co}2] and [{(η5-Cp*)(2-diazo-1,1′,3,3′-tetramethylcyclohexane) Co}2], respectively. In the reaction of 1b with elemental sulfur the formation of a tetranuclear Co-sulfide cluster is observed. In the majority of the reactions studied, l b looses its toluene ligand already at room temperature indicating an unusual high and hitherto unprecedented reactivity of an arene triple decker complex.

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3

Empel, Claire, and Rene M. Koenigs. "Sustainable Carbene Transfer Reactions with Iron and Light." Synlett 30, no. 17 (June 26, 2019): 1929–34. http://dx.doi.org/10.1055/s-0037-1611874.

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Carbenes are versatile, highly reactive intermediates with great importance in chemistry. We recently reported on our findings on safe and scalable applications of hazardous diazoacetonitrile using cheap and commercially available iron catalysts in efficient carbene transfer reactions, ranging from cyclopropanation towards C–H functionalization reactions for the synthesis of biologically important building blocks. More lately, we uncovered the reactivity of diazoalkanes under photochemical conditions using visible light and were able to demonstrate a variety of different, metal-free carbene transfer reactions, which now open up new sustainable ways for the construction of small functional molecules.1 Introduction2 Iron-Catalyzed Carbene Transfer Reactions of Diazoacetonitrile3 Metal-free Carbene Transfer Reaction with Visible Light4 Summary

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4

Zarkesh, Ryan A., and Alan F. Heyduk. "Reactivity of Diazoalkanes with Tantalum(V) Complexes of a Tridentate Amido-Bis(phenolate) Ligand." Organometallics 28, no. 23 (December 14, 2009): 6629–31. http://dx.doi.org/10.1021/om900701n.

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5

Domingo, Luis R., Mar Ríos-Gutiérrez, and Nivedita Acharjee. "Unveiling the Unexpected Reactivity of Electrophilic Diazoalkanes in [3+2] Cycloaddition Reactions within Molecular Electron Density Theory." Chemistry 3, no. 1 (January 10, 2021): 74–93. http://dx.doi.org/10.3390/chemistry3010006.

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The [3+2] cycloaddition (32CA) reactions of strongly nucleophilic norbornadiene (NBD), with simplest diazoalkane (DAA) and three DAAs of increased electrophilicity, have been studied within the Molecular Electron Density Theory (MEDT) at the MPWB1K/6-311G (d,p) computational level. These pmr-type 32CA reactions follow an asynchronous one-step mechanism with activation enthalpies ranging from 17.7 to 27.9 kcal·mol−1 in acetonitrile. The high exergonic character of these reactions makes them irreversible. The presence of electron-withdrawing (EW) substituents in the DAA increases the activation enthalpies, in complete agreement with the experimental slowing-down of the reactions, but contrary to the Conceptual DFT prediction. Despite the nucleophilic and electrophilic character of the reagents, the global electron density transfer at the TSs indicates rather non-polar 32CA reactions. The present MEDT study establishes the depopulation of the N–N–C core in this series of DAAs with the increase of the EW character of the substituents present at the carbon center is responsible for the experimentally found deceleration.

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6

Domingo, Luis R., Mar Ríos-Gutiérrez, and Nivedita Acharjee. "Unveiling the Unexpected Reactivity of Electrophilic Diazoalkanes in [3+2] Cycloaddition Reactions within Molecular Electron Density Theory." Chemistry 3, no. 1 (January 10, 2021): 74–93. http://dx.doi.org/10.3390/chemistry3010006.

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The [3+2] cycloaddition (32CA) reactions of strongly nucleophilic norbornadiene (NBD), with simplest diazoalkane (DAA) and three DAAs of increased electrophilicity, have been studied within the Molecular Electron Density Theory (MEDT) at the MPWB1K/6-311G (d,p) computational level. These pmr-type 32CA reactions follow an asynchronous one-step mechanism with activation enthalpies ranging from 17.7 to 27.9 kcal·mol−1 in acetonitrile. The high exergonic character of these reactions makes them irreversible. The presence of electron-withdrawing (EW) substituents in the DAA increases the activation enthalpies, in complete agreement with the experimental slowing-down of the reactions, but contrary to the Conceptual DFT prediction. Despite the nucleophilic and electrophilic character of the reagents, the global electron density transfer at the TSs indicates rather non-polar 32CA reactions. The present MEDT study establishes the depopulation of the N–N–C core in this series of DAAs with the increase of the EW character of the substituents present at the carbon center is responsible for the experimentally found deceleration.

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7

Werner, Helmut, Norbert Mahr, Justin Wolf, Arno Fries, Matthias Laubender, Elke Bleuel, Raquel Garde, and Pascual Lahuerta. "Synthesis, Molecular Structure, and Reactivity of Rhodium(I) Complexes with Diazoalkanes and Related Substrates as Ligands." Organometallics 22, no. 17 (August 2003): 3566–76. http://dx.doi.org/10.1021/om0302037.

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8

Jefferson, E. A., A. J. Kresge, and S. W. Paine. "Acid-catalyzed hydrolysis of 4-diazo-3-isochromanone: the effect of coplanarity on the carbon protonation of α-phenyl-α-carbonyldiazo compounds." Canadian Journal of Chemistry 74, no. 7 (July 1, 1996): 1369–72. http://dx.doi.org/10.1139/v96-154.

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Hydrolysis of the cyclic α-phenyl-α-carbonyl-diazo compound, 4-diazo-3-isochromanone, in dilute aqueous perchloric acid solutions was found to give the hydronium ion isotope effect [Formula: see text] which shows that this reaction occurs by rate-determining hydronation of the substrate on the carbon atom α to its diazo group. Comparison of the rate constant obtained, [Formula: see text] with that for the corresponding acyclic analog, methyl phenyldiazoacetate, indicates that the cyclic compound is 57 times less reactive. Semi-empirical AM1 molecular orbital calculations suggest that this difference in reactivity is caused by enforced near-coplanarity of the diazo and phenyl groups in the cyclic substrate, as opposed to a staggered arrangement of these groups in the acyclic analog; this coplanarity then enhances delocalization of negative charge from the diazo α-carbon atom into the phenyl group, which reduces the negative charge density on the α-carbon atom and slows the rate of reaction. Key words: hydrolysis, diazoalkanes, charge delocalization, AM1 calculations.

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9

Jefferson, E. A., A. J. Kresge, and S. W. Paine. "Acid-catalyzed hydrolysis of 4-diazo-isothiochroman-3-one. Comparison with the acyclic analog and the corresponding oxygen system." Canadian Journal of Chemistry 75, no. 1 (January 1, 1997): 56–59. http://dx.doi.org/10.1139/v97-008.

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The acid-catalyzed hydrolysis of the cyclic diazothiolactone, 4-diazoisochroman-3-one (3) was found to occur with the hydronium-ion isotope effect, [Formula: see text] and to give the ring-contracted product, 1,3-dihydrobenzo[c]thiophene-1-carboxylic acid (4). This shows that protonation of the diazo carbon atom occurs in the rate-determining step and that the reaction also involves migration of the thio group. The hydronium-ion catalytic coefficient for this reaction, [Formula: see text], is 45 times less than that for hydrolysis of its acyclic thio ester analog, S-methyl phenyldiazothioacetate (5). Semiempirical AM1 molecular orbital calculations support the idea that this difference in reactivity is the result of increased delocalization of negative charge into the aromatic ring in the case of the cyclic substrate, which reduces the negative charge on the diazo carbon atom and makes it less susceptible to protonation. Key words: hydrolysis, diazoalkanes, charge delocalization, AM1 calculations, thio group migration.

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10

Ren, Wenshan, Enwei Zhou, Bo Fang, Guohua Hou, Guofu Zi, De-Cai Fang, and Marc D. Walter. "Experimental and Computational Studies on the Reactivity of a Terminal Thorium Imidometallocene towards Organic Azides and Diazoalkanes." Angewandte Chemie 126, no. 42 (August 28, 2014): 11492–96. http://dx.doi.org/10.1002/ange.201406191.

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11

Ren, Wenshan, Enwei Zhou, Bo Fang, Guohua Hou, Guofu Zi, De-Cai Fang, and Marc D. Walter. "Experimental and Computational Studies on the Reactivity of a Terminal Thorium Imidometallocene towards Organic Azides and Diazoalkanes." Angewandte Chemie International Edition 53, no. 42 (August 28, 2014): 11310–14. http://dx.doi.org/10.1002/anie.201406191.

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12

Bethell, Donald, Sara F. C. Dunn, Medhi M. Khodaei, and A. Raymond Newall. "A kinetic study of the reaction of diazoalkanes with triphenylphosphine: structure and reactivity in a biphilic process." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (1989): 1829. http://dx.doi.org/10.1039/p29890001829.

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13

Dzhemilev, U. M., V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Yu V. Tomilov, and A. B. Kostitsyn. "Reaction of diazoalkanes with unsaturated compounds. 11. Relative reactivity of olefins on catalytic cyclopropanation with diazomethane and palladium catalysts." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 10 (October 1992): 1846–52. http://dx.doi.org/10.1007/bf00863821.

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14

Werner, Helmut, Norbert Mahr, Michael E. Schneider, Marco Bosch, and Justin Wolf. "Acetylacetonato, pentachlorophenolato and carboxylato rhodium(I) complexes and their reactivity in the C–C coupling reaction of olefins and diazoalkanes." Polyhedron 23, no. 17 (November 2004): 2645–57. http://dx.doi.org/10.1016/j.poly.2004.06.009.

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15

Kurup, Sudheer S., Richard J. Staples, Richard L. Lord, and Stanislav Groysman. "Synthesis of Chromium(II) Complexes with Chelating Bis(alkoxide) Ligand and Their Reactions with Organoazides and Diazoalkanes." Molecules 25, no. 2 (January 9, 2020): 273. http://dx.doi.org/10.3390/molecules25020273.

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Synthesis of new chromium(II) complexes with chelating bis(alkoxide) ligand [OO]Ph (H2[OO]Ph = [1,1′:4′,1′’-terphenyl]-2,2′’-diylbis(diphenylmethanol)) and their subsequent reactivity in the context of catalytic production of carbodiimides from azides and isocyanides are described. Two different Cr(II) complexes are obtained, as a function of the crystallization solvent: mononuclear Cr[OO]Ph(THF)2 (in toluene/THF, THF = tetrahydrofuran) and dinuclear Cr2([OO]Ph)2 (in CH2Cl2/THF). The electronic structure and bonding in Cr[OO]Ph(THF)2 were probed by density functional theory calculations. Isolated Cr2([OO]Ph)2 undergoes facile reaction with 4-MeC6H4N3, 4-MeOC6H4N3, or 3,5-Me2C6H3N3 to yield diamagnetic Cr(VI) bis(imido) complexes; a structure of Cr[OO]Ph(N(4-MeC6H4))2 was confirmed by X-ray crystallography. The reaction of Cr2([OO]Ph)2 with bulkier azides N3R (MesN3, AdN3) forms paramagnetic products, formulated as Cr[OO]Ph(NR). The attempted formation of a Cr–alkylidene complex (using N2CPh2) instead forms chromium(VI) bis(diphenylmethylenehydrazido) complex Cr[OO]Ph(NNCPh2)2. Catalytic formation of carbodiimides was investigated for the azide/isocyanide mixtures containing various aryl azides and isocyanides. The formation of carbodiimides was found to depend on the nature of organoazide: whereas bulky mesitylazide led to the formation of carbodiimides with all isocyanides, no carbodiimide formation was observed for 3,5-dimethylphenylazide or 4-methylphenylazide. Treatment of Cr2([OO]Ph)2 or H2[OO]Ph with NO+ leads to the formation of [1,2-b]-dihydroindenofluorene, likely obtained via carbocation-mediated cyclization of the ligand.

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16

Kayen, A. H. M., and Th J. de Boer. "C-Nitroso compounds. Part XXVIII: Generation and reactivity of N-(1-chloroalkyl)nitrones obtained by reaction of diazoalkanes with gem-chloronitroso compounds." Recueil des Travaux Chimiques des Pays-Bas 96, no. 1 (September 2, 2010): 8–12. http://dx.doi.org/10.1002/recl.19770960103.

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17

Albertin, Gabriele, Stefano Antoniutti, Marco Bortoluzzi, Alessandra Botter, Jesús Castro, and Francesca Sibilla. "Preparation of diazoalkane complexes of iron(ii)." RSC Advances 6, no. 100 (2016): 97650–58. http://dx.doi.org/10.1039/c6ra22051g.

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18

Albertin, Gabriele, Stefano Antoniutti, Jesús Castro, and Francesca Sibilla. "Pentamethylcyclopentadienyl osmium complexes that contain diazoalkane, dioxygen and allenylidene ligands: preparation and reactivity." Dalton Transactions 48, no. 9 (2019): 3116–31. http://dx.doi.org/10.1039/c9dt00223e.

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The preparation and reactivity of a series of half-sandwich pentamethylcyclopentadienyl complexes of osmium containing diazoalkane, alkene, dioxygen, vinylidene and allenylidene ligands are described.

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19

Albertin, Gabriele, Stefano Antoniutti, Jesús Castro, and Gianluca Dottorello. "Preparation and reactivity of diazoalkane complexes of ruthenium stabilised by an indenyl ligand." Dalton Transactions 44, no. 19 (2015): 9289–303. http://dx.doi.org/10.1039/c5dt00755k.

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20

Russell, Sarah K., Jordan M. Hoyt, Suzanne C. Bart, Carsten Milsmann, S. Chantal E. Stieber, Scott P. Semproni, Serena DeBeer, and Paul J. Chirik. "Synthesis, electronic structure and reactivity of bis(imino)pyridine iron carbene complexes: evidence for a carbene radical." Chem. Sci. 5, no. 3 (2014): 1168–74. http://dx.doi.org/10.1039/c3sc52450g.

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21

Graham, Todd W., Konstantin A. Udachin, and Arthur J. Carty. "Reactivity patterns of thermally stable, terminal, electrophilic phosphinidene complexes towards diazoalkanes: oxidation at the phosphorus centre and formation of P-bound η1-phosphaazine, η1-phosphaalkene and η3-diazaphosphaallene complexes." Chemical Communications, no. 47 (2005): 5890. http://dx.doi.org/10.1039/b512375e.

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22

Gao, Yuan, Michael C. Jennings, Richard J. Puddephatt, and Hilary A. Jenkins. "Synthesis and Reactivity of a Diruthenium Diazoalkane Complex." Organometallics 20, no. 16 (August 2001): 3500–3509. http://dx.doi.org/10.1021/om0102293.

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23

Albertin, Gabriele, Stefano Antoniutti, Marco Bortoluzzi, Alessandra Botter, and Jesús Castro. "Pentamethylcyclopentadienyl Half-Sandwich Diazoalkane Complexes of Ruthenium: Preparation and Reactivity." Inorganic Chemistry 55, no. 11 (May 17, 2016): 5592–602. http://dx.doi.org/10.1021/acs.inorgchem.6b00671.

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24

Akita, Munetaka, Ruimao Hua, Sadahiro Nakanishi, Masako Tanaka, and Yoshihiko Moro-oka. "Synthesis and Reactivity of Labile MeCN Adducts of Diruthenium Bis(μ-methylene) Species, Cp2Ru2(μ-CH2)2(CO)n(MeCN)2-n(n= 1, 2): Reaction with H Sources, H−X (X = SiR3, SnR3, H), and C−C Coupling with Alkynes and Diazoalkanes." Organometallics 16, no. 25 (December 1997): 5572–84. http://dx.doi.org/10.1021/om9706727.

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25

Albertin, Gabriele, Stefano Antoniutti, Marco Bortoluzzi, Alessandra Botter, and Jesús Castro. "Reactivity with alkene and alkyne of pentamethylcyclopentadienyl half-sandwich diazoalkane complexes of ruthenium." Journal of Organometallic Chemistry 822 (November 2016): 259–68. http://dx.doi.org/10.1016/j.jorganchem.2016.07.016.

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26

Aliev, Z. G., A. M. Sipyagin, V. G. Kartsev, and L. O. Atovmyan. "Structure and reactivity of 3- and 4-[(4?-chlorophenyl)sulfamoyl]-1-diazoalkan-2-ones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 35, no. 1 (January 1986): 120–24. http://dx.doi.org/10.1007/bf00952857.

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27

Polse, Jennifer L., Anne W. Kaplan, Richard A. Andersen, and Robert G. Bergman. "Synthesis of an η2-N2-Titanium Diazoalkane Complex with Both Imido- and Metal Carbene-Like Reactivity Patterns." Journal of the American Chemical Society 120, no. 25 (July 1998): 6316–28. http://dx.doi.org/10.1021/ja974303d.

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28

Polse, Jennifer L., Richard A. Andersen, and Robert G. Bergman. "Synthesis, Structure, and Reactivity Studies of an η2-N2-Titanium Diazoalkane Complex. Generation and Trapping of a Carbene Complex Intermediate." Journal of the American Chemical Society 118, no. 36 (January 1996): 8737–38. http://dx.doi.org/10.1021/ja9614981.

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29

Zhang, Jing, Mark Gandelman, Linda J. W. Shimon, and David Milstein. "Stable Carbene and Diazoalkane Complexes of the Same Complex System. Synthesis, Structure, and Reactivity of PNP−Ru(II) Fluorenylidene and Diazofluorene Complexes." Organometallics 27, no. 14 (July 2008): 3526–33. http://dx.doi.org/10.1021/om800294v.

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30

Graham, Todd W., Konstantin A. Udachin, and Arthur J. Carty. "Reactivity of electrophilic µ-phosphinidene complexes with heterocumulenes: formation of the first σ-π-aminophosphaimine complexes [Mn2(CO)8{µ-η1,η2-P(NiPr2)NR}] and diazoalkane insertions into metal–phosphorus bonds." Chemical Communications, no. 35 (2005): 4441. http://dx.doi.org/10.1039/b505472a.

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31

BETHELL, D., S. F. C. DUNN, M. M. KHODAEI, and A. R. NEWALL. "ChemInform Abstract: A Kinetic Study of the Reaction of Diazoalkanes with Triphenylphosphine: Structure and Reactivity in a Biphilic Process." ChemInform 21, no. 10 (March 6, 1990). http://dx.doi.org/10.1002/chin.199010237.

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32

Domingo, Luis R., and Nivedita Acharjee. "Unveiling the high reactivity of strained dibenzocyclooctyne in [3 + 2] cycloaddition reactions with diazoalkanes through the molecular electron density theory." Journal of Physical Organic Chemistry 33, no. 11 (July 16, 2020). http://dx.doi.org/10.1002/poc.4100.

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