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Journal articles on the topic 'Oxaziridine chemistry'

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1

Meladinis, Vassilios, Uwe Verfürth, and Rudolf Herrmann. "Highly Efficient Camphor-Derived Oxaziridines for the Asymmetric Oxidation of Sulfides to Chiral Sulfoxides." Zeitschrift für Naturforschung B 45, no. 12 (December 1, 1990): 1689–94. http://dx.doi.org/10.1515/znb-1990-1216.

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Chiral N-sulfonyl-oxaziridines derived from 8-camphorsulfonic acid and fenchone have been evaluated as asymmetric oxidizing agents for the conversion of sulfides to chiral sulfoxides. There is no correlation between the redox potentials nor the 17O NMR chemical shifts of the oxaziridines and their relative oxidation rates, nor with the enantiomeric excesses achieved, indicating that steric effects are responsible for their behaviour. The results are consistent with an attack of one sulfur lone pair at the oxaziridine oxygen in such a way that both sulfur lone pairs lie in the plane of the oxaziridine ring. The most efficient oxaziridines, the camphorlactone-sulfonyloxaziridine [(4aS,9 aR)-10,10-dimethyl-6,7-dihydro-4 H-4 a,7-methano-oxazirino[3,2-j]oxepino[3,4-c]isothiazol-9(5H)-one 3,3-dioxide] and the 3-endo-bromocamphorsulfonyloxaziridine [(4aS,8 S,8 aR)-8-bromo-9,9-dimethyl-5,6,7,8-tetrahydro-4 H- 4a,7-methano-oxazirino-2,1-benzisothiazole 3,3-dioxide] allow the preparation of chiral sulfoxides with up to 85% enantiomeric excess.
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2

Davis, Franklin A., James C. Towson, Michael C. Weismiller, Sankar Lal, and Patrick J. Carroll. "Chemistry of oxaziridines. 11. (Camphorylsulfonyl)oxaziridine: synthesis and properties." Journal of the American Chemical Society 110, no. 25 (December 1988): 8477–82. http://dx.doi.org/10.1021/ja00233a025.

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3

Wagner, Gabriele, Uwe Verfürth, and Rudolf Herrmann. "Chemistry of Fenchonesulfonic Acid Derivatives." Zeitschrift für Naturforschung B 50, no. 2 (February 1, 1995): 283–88. http://dx.doi.org/10.1515/znb-1995-0223.

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(1 S) - (+)-Fenchone is sulfonated by SO3 or H2SO4/acetic anhydride in the bridgehead methyl group. This could be confirmed by NMR techniques (INADEQUATE). The fenchonesulfonic acid obtained is converted (SOCl2/NH3) to the cyclic fenchonesulfonimide, which can be oxidized to the corresponding oxaziridine, in close analogy to 10-camphorsulfonimide. Improved procedures for this reaction sequences are given. During the treatment of the sulfonic acid with thionyl chloride, a byproduct with a rearranged bicyclic skeleton is observed whose structure has been determined by ozonolytic degradation and NMR techniques. A possible mechanism for this rearrangement is suggested, based on MNDO calculations of the intermediate carbocations. The fenchonesulfonyloxaziridine oxidizes sulfides to chiral sulfoxides with appreciable enantiomeric excess, but very low reaction rate. A comparison with camphor-derived oxaziridines having similar steric requirements is made.
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4

Elledge, Susanna K., Hai L. Tran, Alec H. Christian, Veronica Steri, Byron Hann, F. Dean Toste, Christopher J. Chang, and James A. Wells. "Systematic identification of engineered methionines and oxaziridines for efficient, stable, and site-specific antibody bioconjugation." Proceedings of the National Academy of Sciences 117, no. 11 (March 2, 2020): 5733–40. http://dx.doi.org/10.1073/pnas.1920561117.

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The field of chemical modification of proteins has been dominated by random modification of lysines or more site-specific labeling of cysteines, each with attendant challenges. Recently, we have developed oxaziridine chemistry for highly selective modification of methionine called redox-activated chemical tagging (ReACT) but have not broadly tested the molecular parameters for efficient and stable protein modification. Here we systematically scanned methionines throughout one of the most popular antibody scaffolds, trastuzumab, used for antibody engineering and drug conjugation. We tested the expression, reactivities, and stabilities of 123 single engineered methionines distributed over the surface of the antibody when reacted with oxaziridine. We found uniformly high expression for these mutants and excellent reaction efficiencies with a panel of oxaziridines. Remarkably, the stability to hydrolysis of the sulfimide varied more than 10-fold depending on temperature and the site of the engineered methionine. Interestingly, the most stable and reactive sites were those that were partially buried, presumably because of their reduced access to water. There was also a 10-fold variation in stability depending on the nature of the oxaziridine, which was determined to be inversely correlated with the electrophilic nature of the sulfimide. Importantly, the stabilities of the best analogs were sufficient to support their use as antibody drug conjugates and potent in a breast cancer mouse xenograft model over a month. These studies provide key parameters for broad application of ReACT for efficient, stable, and site-specific antibody and protein bioconjugation to native or engineered methionines.
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5

Davis, Franklin A., Aurelia C. Sheppard, Bang Chi Chen, and M. Serajul Haque. "Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine." Journal of the American Chemical Society 112, no. 18 (August 1990): 6679–90. http://dx.doi.org/10.1021/ja00174a035.

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6

Meladinis, Vassilios, Rudolf Herrmann, Oliver Steigelmann, and Gerhard Müller. "Synthesis and Structure of a New Chiral Oxaziridine from (3-Oxo-camphorsulfonyl)imine." Zeitschrift für Naturforschung B 44, no. 11 (November 1, 1989): 1453–58. http://dx.doi.org/10.1515/znb-1989-1122.

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Oxidation of (3-oxo-camphorsulfonyl)imine (1) by magnesium monoperoxyphthalate does not lead to the oxaziridine obtained with 3-chloro-perbenzoic acid, but to a new chiral oxaziridine containing an additional oxygen atom (Baeyer-Villiger type oxidation). The structure of the product is established by X-ray crystallography, and reaction pathways for the oxidation of 1 by peracids are discussed.
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7

Armstrong, Alan, Ian D. Edmonds, Martin E. Swarbrick, and Nigel R. Treweeke. "Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions." Tetrahedron 61, no. 35 (August 2005): 8423–42. http://dx.doi.org/10.1016/j.tet.2005.06.085.

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8

Pointner, Andreas, and Rudolf Herrmann. "Transition State Geometry and Solvent Effects in the Enantioselective Oxidation of Sulfides to Chiral Sulfoxides by Oxaziridines." Zeitschrift für Naturforschung B 50, no. 9 (September 1, 1995): 1396–403. http://dx.doi.org/10.1515/znb-1995-0917.

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AbstractFor the enantioselective oxidation of methyl phenyl sulfide and tert-butyl methyl sulfide to the corresponding chiral sulfoxides by 3,3-dibromo-(camphorsulfonyl)oxaziridine, semiempirical calculations (MNDO, AMI, PM3) concerning transition state geometries were performed. The results show that only PM3 is able to localize a transition state. For methyl phenyl sulfide, a spiro arrangement of the oxaziridine ring and the sulfur atom explains the observed direction of the selectivity better than a planar transition state. The solvent dependence of the observed enantioselectivity is related to the calculated dipole moment of the transition state by the Kirkwood-Onsager model. In THF as solvent, its direct participation in the transition state has to be considered
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9

Dickmeis, Marcus, Hakan Cinar, and Helmut Ritter. "Macrocyclic and Polymeric Oxaziridine-Derivatives." Macromolecular Rapid Communications 34, no. 3 (January 11, 2013): 263–68. http://dx.doi.org/10.1002/marc.201200706.

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10

Singh, Santosh K., Jesse La Jeunesse, Cheng Zhu, N. Fabian Kleimeier, Kuo-Hsin Chen, Bing-Jian Sun, Agnes H. H. Chang, and Ralf I. Kaiser. "Gas phase identification of the elusive oxaziridine (cyclo-H2CONH) – an optically active molecule." Chemical Communications 56, no. 100 (2020): 15643–46. http://dx.doi.org/10.1039/d0cc06760a.

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11

Miranda, Margarida S., Paulo J. O. Ferreira, Joaquim C. G. Esteves da Silva, and Joel F. Liebman. "Three-membered ring amides — a calculational and conceptual study of the structure and energetics of 1,2-oxaziridine-3-one and aziridine-2,3-dione." Canadian Journal of Chemistry 93, no. 4 (April 2015): 406–13. http://dx.doi.org/10.1139/cjc-2014-0321.

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Species with three-membered rings and the amide linkage are well studied. A quick perusal of the literature with SciFinder finds some 50 000 references to cyclopropanes and almost 300 000 references to amides. In the current paper, we discuss the structure and energetics of two understudied three-membered ring amides, 1,2-oxaziridine-3-one (5) (simultaneously describable as the simplest cyclic carbamate and simplest hydroxamate) and aziridine-2,3-dione (7) (simultaneously describable as the simplest imide and simplest α-ketoamide), with but 5 and nearly 10 references, respectively, for these two classes of compounds. Neither 1,2-oxaziridine-3-one (5) nor aziridine-2,3-dione (7), nor any derivative thereof, has been isolated. Calculational theory ameliorates the paucity of experimental information. The current study reports our computational findings for these and related species (e.g., enols and imidols) where we have used the G3(MP2)//B3LYP method.
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12

Šnajdr, Ivan, Jordan Froese, Travis Dudding, Pavlína Horáková, and Tomáš Hudlický. "Investigation of a new chiral auxiliary derived chemoenzymatically from toluene: experimental and computational study." Canadian Journal of Chemistry 94, no. 10 (October 2016): 848–56. http://dx.doi.org/10.1139/cjc-2016-0327.

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A tricyclic chiral auxiliary, prepared from the enzymatically derived cis-arene dihydrodiol metabolite of toluene, was investigated as a means of asymmetric induction in several different reactions. The auxiliary was converted to an oxaziridine, and its utility in hydroxylation, providing low levels of enantiomeric excess, was compared with that of Davis’s oxaziridine. Insight into the origin of stereoinduction in this reaction is provided and is based on computational Monte Carlo Multiple Minimum (MCMM) searches using the OPLS3 force field. The use of the auxiliary group in the alkylation of appended esters proved disappointing. Diels-Alder cycloaddition of an acrylate, derived from the auxiliary group, with cyclohexadiene furnished a mixture of diastereomeric adducts in essentially equal amounts. The adducts were separated and the corresponding enantiomeric residues were isolated with good enantiomeric excess. Evidence of reasonable levels of asymmetric induction in the above processes was lacking. Experimental and spectral data are provided for all key compounds.
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13

Stumpf, Renate, and Peter Lemmen. "Syntheses of Phospholipids via Oxazaphospholanes." Zeitschrift für Naturforschung B 45, no. 12 (December 1, 1990): 1729–32. http://dx.doi.org/10.1515/znb-1990-1221.

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A method for the synthesis of the head group of phospholipids is described. It is formed by ring opening of oxazaphospholanes, either by mild tetrazole mediated hydrolysis of λ3-oxazaphospholanes or by methylating ring cleavage of λ5-oxazaphospholanes. Oxidation can be performed by means of an oxaziridine.
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14

Davis, Franklin A., R. Thimma Reddy, Wei Han, and Patrick J. Carroll. "Chemistry of oxaziridines. 17. N-(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: a highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides." Journal of the American Chemical Society 114, no. 4 (February 1992): 1428–37. http://dx.doi.org/10.1021/ja00030a045.

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15

Behnke, Nicole Erin, Russell Kielawa, Doo-Hyun Kwon, Daniel H. Ess, and László Kürti. "Direct Primary Amination of Alkylmetals with NH-Oxaziridine." Organic Letters 20, no. 24 (December 10, 2018): 8064–68. http://dx.doi.org/10.1021/acs.orglett.8b03734.

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16

Aly, Ashraf A., Alaa A. Hassan, and Aboul-Fetouh E. Mourad. "Novel [2.2]paracyclophane derivatives via charge-transfer complexation." Canadian Journal of Chemistry 71, no. 11 (November 1, 1993): 1845–49. http://dx.doi.org/10.1139/v93-231.

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The transannular electronic interactions in [2.2]paracyclophanes affect the selectivity of the tricyanovinylation reaction with tetracyanoethylene (TCNE). In addition to the normal N-tricyanovinyl product, 4-amino[2,2]paracyclophane reacts with TCNE to give oxaziridine derivatives. In the case of reaction with 4-N-methylamino[2.2]paracyclophane, the unusual N-tricyanovinylated product as well as 4-(N-carbonitrile-N-methyl)annino[2.2]paracyclophane was isolated. The reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 4-amino[2.2]paracyclophane results in formation of 2-cyano-3-(4-[2.2]paracyclophanyl)amino-5,6-dichloro-1,4-benzoquinone.
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17

Usuki, Yoshinosuke, Xin Peng, Belgin Gülgeze, and Jeffrey Aubé. "Cyclization of a carbon-centered radical derived from oxaziridine cleavage." Arkivoc 2006, no. 4 (April 27, 2006): 189–99. http://dx.doi.org/10.3998/ark.5550190.0007.413.

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18

DAVIS, F. A., R. T. REDDY, W. HAN, and P. J. CARROLL. "ChemInform Abstract: Chemistry of Oxaziridines. Part 17. N-(Phenylsulfonyl)(3,3- dichlorocamphoryl)oxaziridine: A Highly Efficient Reagent for the Asymmetric Oxidation of Sulfides to Sulfoxides." ChemInform 23, no. 21 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199221112.

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19

Davis, Franklin A., Anil Kumar, and Bang Chi Chen. "Chemistry of oxaziridines. 16. A short, highly enantioselective synthesis of the AB-ring segments of .gamma.-rhodomycionone and .alpha.-citromycinone using (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine." Journal of Organic Chemistry 56, no. 3 (February 1991): 1143–45. http://dx.doi.org/10.1021/jo00003a042.

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20

Allen, Charles P., Tamas Benkovics, Amanda K. Turek, and Tehshik P. Yoon. "Oxaziridine-Mediated Intramolecular Amination of sp3-Hybridized C−H Bonds." Journal of the American Chemical Society 131, no. 35 (September 9, 2009): 12560–61. http://dx.doi.org/10.1021/ja906183g.

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21

Beak, Peter, David R. Anderson, Stephen G. Jarboe, Mitchell L. Kurtzweil, and Keith W. Woods. "Mechanisms and consequences of oxygen transfer reactions." Pure and Applied Chemistry 72, no. 12 (January 1, 2000): 2259–64. http://dx.doi.org/10.1351/pac200072122259.

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The geometry about oxygen in the transition-state structures for oxygen transfers from a nitrone to phosphorous, from a percarboxylic acid to a carbon­carbon double bond, and from an N-sulfonyl oxaziridine to a carbon­carbon double bond have been evaluated by the endocyclic restriction test. The former can proceed at an oblique angle, while the latter two require a large angle between the entering and leaving groups on oxygen. This information is used to determine the mechanism of the aldehyde-dependent oxygen transfer from molecular oxygen to a carbon­carbon double bond.
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22

Troisi, Luigino, Valeria Videtta, Serena Perrone, Francesca Rosato, Pietro Alifano, and Salvatore Tredici. "Condensed Oxaziridine-Mediated [3+2] Cycloaddition: Synthesis of Polyhetero-bicyclo Compounds." Synlett 2010, no. 18 (October 8, 2010): 2781–83. http://dx.doi.org/10.1055/s-0030-1258819.

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23

Hilinski, Michael, Shea Johnson, and Logan Combee. "Organocatalytic Atom-Transfer C(sp3)–H Oxidation." Synlett 29, no. 18 (June 27, 2018): 2331–36. http://dx.doi.org/10.1055/s-0037-1610432.

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Predictably site-selective catalytic methods for intermolecular C(sp3)–H hydroxylation and amination hold great promise for the synthesis and late-stage modification of complex molecules. Transition-metal catalysis has been the most common approach for early investigations of this type of reaction. In comparison, there are far fewer ­reports of organocatalytic methods for direct oxygen or nitrogen insertion into C–H bonds. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of an iminium salt that catalyzes both oxygen and nitrogen insertion.1 Introduction2 Background: C–H Oxidation Capabilities of Heterocyclic Oxidants3 Oxaziridine-Mediated Catalytic Hydroxylation4 Dioxirane-Mediated Catalytic Hydroxylation5 Iminium Salt Catalysis of Hydroxylation and Amination6 Conclusion and Outlook
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24

Susanto, Woen, and Yulin Lam. "Oxidation reactions using polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine." Tetrahedron 67, no. 43 (October 2011): 8353–59. http://dx.doi.org/10.1016/j.tet.2011.08.058.

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25

Falah, Samah, Fatma Abdmouleh, Rihab Aydi, Besma Hamdi, Mehdi El Arbi, and Majed Kammoun. "Synthesis, crystal structure study, and antimicrobial evaluation activity of aryl-substituted dihydroisoquinoline oxaziridine." Journal of Molecular Structure 1205 (April 2020): 127592. http://dx.doi.org/10.1016/j.molstruc.2019.127592.

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26

Davis, Franklin A., John P. McCauley, Sankar Chattopadhyay, Mark E. Harakal, James C. Towson, William H. Watson, and Iraj Tavanaiepour. "Chemistry of oxaziridines. 8. Asymmetric oxidation of nonfunctionalized sulfides to sulfoxides with high enantioselectivity by 2-sulfamyloxaziridines. Influence of the oxaziridine C-aryl group on the asymmetric induction." Journal of the American Chemical Society 109, no. 11 (May 1987): 3370–77. http://dx.doi.org/10.1021/ja00245a030.

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27

Davis, Franklin A., and Michael C. Weismiller. "Enantioselective synthesis of tertiary .alpha.-hydroxy carbonyl compounds using [(8,8-dichlorocamphoryl)sulfonyl]oxaziridine." Journal of Organic Chemistry 55, no. 12 (June 1990): 3715–17. http://dx.doi.org/10.1021/jo00299a007.

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28

DAVIS, F. A., A. KUMAR, and B. C. CHEN. "ChemInform Abstract: Chemistry of Oxaziridines. Part 16. A Short, Highly Enantioselective Synthesis of the AB-Ring Segments of γ-Rhodomycinone and α- Citromycinone Using (+)-((8,8-Dimethoxycamphoryl)sulfonyl)oxaziridine." ChemInform 22, no. 27 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199127068.

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29

Brodsky, Benjamin H., and J. Du Bois. "Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C−H Bonds Using Hydrogen Peroxide." Journal of the American Chemical Society 127, no. 44 (November 2005): 15391–93. http://dx.doi.org/10.1021/ja055549i.

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30

Wang, Chen, Yuan-Ye Jiang, and Chen-Ze Qi. "Mechanism and Origin of Chemical Selectivity in Oxaziridine-Based Methionine Modification: A Computational Study." Journal of Organic Chemistry 82, no. 18 (September 6, 2017): 9765–72. http://dx.doi.org/10.1021/acs.joc.7b02026.

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31

Caupène, Caroline, Claudie Martin, Margareth Lemarié, Stéphane Perrio, and Patrick Metzner. "Mild and efficient access to lithium alkanesulfinates based on oxaziridine-promoted oxidation of thiolates." Journal of Sulfur Chemistry 30, no. 3-4 (June 29, 2009): 338–45. http://dx.doi.org/10.1080/17415990902903009.

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32

Verfürth, Uwe, and Ivar Ugi. "Asymmetrische Synthese chiraler Phosphorverbindungen durch destruktiv-Oxidation von P(III)-Verbindungen mittels chiraler Oxaziridine." Chemische Berichte 124, no. 7 (July 1991): 1627–34. http://dx.doi.org/10.1002/cber.19911240725.

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33

Bach, Robert D., Jose L. Andres, and Franklin A. Davis. "Mechanism of oxygen atom transfer from oxaziridine to a lithium enolate. A theoretical study." Journal of Organic Chemistry 57, no. 2 (January 1992): 613–18. http://dx.doi.org/10.1021/jo00028a039.

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34

Michaelis, David J., Kevin S. Williamson, and Tehshik P. Yoon. "Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes." Tetrahedron 65, no. 26 (June 2009): 5118–24. http://dx.doi.org/10.1016/j.tet.2009.03.012.

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35

Enders, Dieter, Christine Poiesz, and Reni Joseph. "Enantioselective synthesis of protected α-aminoketones via electrophilic amination of α-silylketones with an oxaziridine." Tetrahedron: Asymmetry 9, no. 20 (October 1998): 3709–16. http://dx.doi.org/10.1016/s0957-4166(98)00382-6.

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36

Kammoun, Majed, Ridha Ben Salem, and Mohamed Damak. "Acid-Promoted Oxygen-Atom Transfer from a Novel Dihydroisoquinoline-Derived Oxaziridine Substituted at Position 1." Synthetic Communications 42, no. 15 (April 9, 2012): 2181–90. http://dx.doi.org/10.1080/00397911.2011.555050.

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37

Mahale, Rajendra D., Mahesh R. Rajput, Golak C. Maikap, and Mukund K. Gurjar. "Davis Oxaziridine-Mediated Asymmetric Synthesis of Proton Pump Inhibitors Using DBU Salt of Prochiral Sulfide." Organic Process Research & Development 14, no. 5 (September 17, 2010): 1264–68. http://dx.doi.org/10.1021/op100075v.

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38

Sharma, Abha, Amit Saxena, and Beer Singh. "In-situ degradation of sulphur mustard using (1R)-(-)-(camphorylsulphonyl) oxaziridine impregnated adsorbents." Journal of Hazardous Materials 172, no. 2-3 (December 2009): 650–53. http://dx.doi.org/10.1016/j.jhazmat.2009.07.046.

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39

Armstrong, Alan, Lyn H. Jones, Jamie D. Knight, and Richard D. Kelsey. "Oxaziridine-Mediated Amination of Primary Amines: Scope and Application to a One-Pot Pyrazole Synthesis." Organic Letters 7, no. 4 (February 2005): 713–16. http://dx.doi.org/10.1021/ol0474507.

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40

Benkovics, Tamas, Ilia A. Guzei, and Tehshik P. Yoon. "Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantiomerically Enriched 3-Aminopyrroloindolines." Angewandte Chemie International Edition 49, no. 48 (October 21, 2010): 9153–57. http://dx.doi.org/10.1002/anie.201004635.

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41

Peng, Xingao, Yingguang Zhu, Thomas A. Ramirez, Baoguo Zhao, and Yian Shi. "New Reactivity of Oxaziridine: Pd(II)-Catalyzed Aromatic C–H Ethoxycarbonylation via C–C Bond Cleavage." Organic Letters 13, no. 19 (October 7, 2011): 5244–47. http://dx.doi.org/10.1021/ol2021252.

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42

Bragante, Letanzio, and Darryl D. Desmarteau. "The chemistry of 3-trifluoromethyl-perfluoro-aza-2,-butene and the synthesis of a new oxaziridine: 3,3-bistrifluoromethyl,-2-trifluoromethyloxaziridine." Journal of Fluorine Chemistry 53, no. 2 (July 1991): 181–97. http://dx.doi.org/10.1016/s0022-1139(00)82340-4.

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43

BRAGANTE, L., and D. D. DESMARTEAU. "ChemInform Abstract: The Chemistry of 3-Trifluoromethylperfluoroaza-2-butene and the Synthesis of a New Oxaziridine: 3,3-Bistrifluoromethyl-2- trifluoromethyloxaziridine." ChemInform 23, no. 13 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199213186.

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44

Tripolt, Robert, Ferdinand Belaj, and Edgar Nachbaur. "Eine unerwartet stabile Sulfensäure: 4,6-Dimethoxy-1,3,5-triazin-2-sulfensäure; Synthese, Eigenschaften, Molekül- und Kristallstruktur / Unexpectedly Stable Sulfenic Acid: 4,6-Dimethoxy-1,3,5-triazine-2-sulfenic Acid; Synthesis, Properties, Molecular and Crystal Structure." Zeitschrift für Naturforschung B 48, no. 9 (September 1, 1993): 1212–22. http://dx.doi.org/10.1515/znb-1993-0909.

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4,6-Dimethoxy-1,3,5-triazine-2-sulfenic acid (1) was prepared by the reaction of 4,6-dimethoxy-1,3,5-triazine-2(1H)-thion (3) with 2-benzenesulfonyl-3-(p-nitrophenyl)-oxaziridine (2) in THF solution and isolated as a stable crystalline solid. The new compound was characterized by analytical and spectroscopic data (IR, 1H and 13C NMR, UV, MS) supported by MNDO-PM 3 calculations. UV spectrometry was used for exact determination of the ionization constant of 1(pKa = 5.86 ± 0.02 at 20°C). According to 13C NMR data and X-ray analysis the sulfenic acid 1 adopts the sulfenyl structure (R—SOH) in the condensed phase.Crystal data of 1 (90 K): a = 8.418(3), b = 21.289(6), c = 4.411(1) Å, Z = 4, P 21212, R = 0.0304, Rw = 0.0354 for 4105 unique reflections and 122 parameters. In the crystal, the molecules form dimers by two strong intermolecular O—H ••• N hydrogen bonds. The 6-membered ring shows alternating C—N bond lengths and is almost planar. The experimental electron deformation density (EDD) decreases in the order C—N > C—O ≈ C—S > S—O and is described in detail for the vicinity of the S atom.
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45

Bach, Robert D., Barry A. Coddens, Joseph J. W. McDouall, H. Bernhard Schlegel, and Franklin A. Davis. "The mechanism of oxygen transfer from an oxaziridine to a sulfide and a sulfoxide: a theoretical study." Journal of Organic Chemistry 55, no. 10 (May 1990): 3325–30. http://dx.doi.org/10.1021/jo00297a062.

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46

Armstrong, Alan, Lee Challinor, Richard S. Cooke, Jennifer H. Moir, and Nigel R. Treweeke. "Oxaziridine-Mediated Amination of Branched Allylic Sulfides: Stereospecific Formation of Allylic Amine Derivatives via [2,3]-Sigmatropic Rearrangement." Journal of Organic Chemistry 71, no. 10 (May 2006): 4028–30. http://dx.doi.org/10.1021/jo060369s.

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47

Armstrong, Alan, Richard S. Cooke, and Stephen E. Shanahan. "Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine: synthesis of N-allenylsulfenimides." Organic & Biomolecular Chemistry 1, no. 18 (2003): 3142. http://dx.doi.org/10.1039/b307722e.

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48

Shimizu, Masao, Yasuo Gama, and Isao Shibuya. "Reactions of 2-tert-Butyl-3-phenyl-oxaziridine with Alkyl Isothiocyanates and Its Application to Glucosyl-aminoheterocycle Synthesis." HETEROCYCLES 48, no. 9 (1998): 1935. http://dx.doi.org/10.3987/com-98-8261.

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49

Ghosh, Asit, Subhajit Mandal, Pratim Kumar Chattaraj, and Prabal Banerjee. "Ring Expansion of Donor–Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights." Organic Letters 18, no. 19 (September 29, 2016): 4940–43. http://dx.doi.org/10.1021/acs.orglett.6b02417.

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50

Ceruti, Maurizio, Franca Viola, Gianni Balliano, Giorgio Grosa, Otto Caputo, Nicolas Gerst, Francis Schuber, and Luigi Cattel. "Synthesis of a squalenoid oxaziridine and other new classes of squalene derivatives, as inhibitors of sterol biosynthesis." European Journal of Medicinal Chemistry 23, no. 6 (November 1988): 533–37. http://dx.doi.org/10.1016/0223-5234(88)90096-7.

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