Ref.547.2 WAN

Total Page:16

File Type:pdf, Size:1020Kb

Ref.547.2 WAN 3632 SUBJECT INDEX 1,3-dipole, 916, 917,1217, 1504, 1505 2-nitroaniline, 142, 1868 1,3-oxazine, 1913 2-nitrobenzaldehyde, 136 1,3,2-benzothiazathiolium chloride, 1395 2-nitropropane, 1336, 1337 1,3,5-trihydroxybenzene, 1498 2-nonyne, 317 1,4-benzohydroquinone, 1477 2-oxazoline, 2529 1,4-benzoquinone, 1477, 123,2042,2044 2-picoline, 2998 1,4-dimethoxybenzene, 1128 2-pyridinealdoxime, 2734 1,4-dioxygenation, 1675 2-pyrroline, 2529 1,4-hydroquinone, 1055, 1477, 1841 2-tetrahydroxybutyl-quinoxaline, 2084, 2086 1,4-naphthoquinonedibenzene-sulfonimide, 2-thiohydantoin, 2488, 2489, 2490, 2858 2147 2-vinylbutadiene, 1014 1,4-pentadiene, 1519,2881 2-vinyloxetane, 308 1,5-cyclooctadiene,803 2-vinyloxirane, 308 1,6-naphthyridine, 2335 2-vinylphosphirane,2881 1,7-dihydroxynaphthalene, 553 2,2-diethoxypropane, 200 1 1,8-naphthalenediamine,2198 2,2,4,4-tetramethylpiperidine,3146 1,8-naphthyridine, 1138 2,2' -dibenzoyloxyacetophenone, 170 IO-ketodocosanoic acid, 422 2,3,5-triphenylimidazole, 2293 l O-phenanthroline, 1572 2,3,5,6-tetramethylacetophenone, 130 12-ketoergostane, 1857 2,4-dialkoxypyrimidine, 1408 12-ketopregnane, 1857 2,4-dimethylquinoline, 1139 17-hydroxy-20-ketosteroid,877 2,4-dinitrophenylacetone, 2017 17-keto-steroid,3158 2,4-dinitrophenylhydrazine, 1007, 1086, 1633, 17-oxo-steroid, 3158 1847, 1855 18-crown-6, 704, 737, 743, 1250, 1485, 1487, 2,4-dinitrotoluene, 1381, 1895 2008,2550,2782,2848,2976 2,4,6-trinitrotoluene, 1041 IH-l,2,3-triazole,905 2,5-dimethoxytetrahydrofuran, 667, 2415, 2416 2-acetidinethione, 1222 2,6-dinitroisovanillin, 136 2-acetylphenothiazine, 2188 2,6-diphenylmethyltetrahydro-4-pyranone, 2-alkenylthioanilide, 1164 1800 2-alkyloxazoline, 750 2,6-lutidine, 170, 1162, 1735,2462 2-aminopyridine, 631, 632, 753, 2891 2'-deoxyribofuranosylpyrimidine, 1408 2-aminothiophene, 1213, 1214 2'-hydroxychalcone, 53 2-azetidinone, 819, 1234,2636 2'-oxychalcone, 52 2-bromoethylphthalimide, 1178 20-ketopregnane, 2988 2-bromonaphthalene, 1969 2H-azirine, 1376 2-bromopyridine, 513, 753 3-alkoxyacetal, 2000 2-butene-l,4-diol, 1668 3-aminoacenaphthene,690 2-cyclopentenone, 2011 3-aminopyridine, 693, 921 2-hydroxyacetophenone, 54 3-benzyl-5-(2-hydroxyethyl)-4­ 2-hydroxyquinoline,692, 1639 methylthiazolium chloride, 14, 1938, 2-imidazoline, 2529 2665 2-imidazolinone, 2529 3-bromopropyne, 1038 2-iminohydantoin, 954, 955 3-chloroaniline, 907 2-isocyanostyrene, 1164, 1167 3-chloropseudocumene, 1531 2-methoxyquinoline,1713 3-ethylthiotetrahydrofuran, 537 2-methoxythiophene,491 3-furoic acid, 310 1 2-methyl-5-phenylsulfonylhydroquinone, 1422 3-hydroxycinnoline, 2022, 2023 2-methyl-6-phenylsulfonylhydroquinone, 1422 3-hydroxyquinuclidine, 275 2-methylindole, 1358, 1360, 1793 3-iodoanisole, 1912 2-methylterephthalic acid, 1381 3-methylalizarin,461 2-methylthiobenzthiazole, 1714 3-methylcyclohexanol, 119 SUBJECT INDEX 3633 3-methyleneindoline, 1719 acetogenin, 1609 3-methylisocoumarin, 1359 acetohydroxamate, 2489 3-oxoglutarate, 2968 acetolysis, 2931 3-phenylindene, 2884 acetomesitylene, 1750 3-phenylpropionaldehyde, 2175 acetonedicarboxylic ester, 2182 3-picoline, 2998 acetonide, 1279, 1280, 1281 3-quinuclidinone, 2570 acetophenone, 268,598,661,662,677,711, 3-quinuclidone, 275 874,912,995,1316,1675,1739,1860,1862, xaline,2084, 2086 3-thiazoline, 107, 108 2062,2074,2090,2188,2260,2491,2731, 19,2490,2858 3,4-lutidine, 3141 3012,3018,3019,3020,3034,3121,3137 3,5-dicyanodihydropyidine, 1321 acetoxylation, 2762 3,5-dinitrobenzamide, 1543 acetyl hexachloroantimonate, 849 4-aminoindole, 1254 acetyldemissidine, 2896 4-aminophenol, 191 acetylene cyclotrimerization, 2345 1 4-bromoindole, 1361 acetylene-allene rearrangement, 2864 ine,3146 4-ethylpyridine, 2998, 2999 acetylene, 93, 101, 181, 389, 391, 536, 606, enone, 170 4-hydroxyazobenzene, 2942 616,619,621,635,820,1032,1034,1151, 2293 4-hydroxycinnonline,474 1703,1710,1728,1779,2147,2234,2345, lenone, 130 4-hydroxyquinoline, 692, 693, 1252, 1253, 2347,2353,2358,2362,2363,2364,2365, 408 1638 2373,2450,2495,2548,2562,2793,2794, 39 4-iodoacetophenone, 1432, 2631 3018,3019,3020,3021,3148 2017 4-keto-3,4-dihydroquinazoline, 2054 acetylide, 616, 619,1032,2471,2629 ie, 1007, 1086, 1633, 4-methyl-aminoveratrole, 1417 acridine, 362,363, 364,2467, 2468, 2838, 4-nitrobenzenesulfenyl chloride, 70 2839,2872 1895 4-octanone, 677 acridizinium, 506, 511, 5 J2 L 4-picoline, 2482 acridone, 1572, 1731, 1732, 2838 uran, 667, 2415, 2416 4-quinolone, 692 acrolein, 176; 177,178,275,925,1621,1913, ) 4,6-dichlorobenzothiazole, 1395, 1397 2604,2873 ydro-4-pyranone, 5-bromomethylvanillic acid, 1482 acrylonitrile, 275, 919 5-enopyranoside, 1051 acrynitrile, 1908, 2307 735,2462 5-exo-dig radical cyclization, 1167 actinometry, 952, 953 imidine, 1408 5-forrnyl indane, 492 acutiphycin,47 5-hydroxyindole, 2042, 2043 acyclic diene metathesis polymerization, 57 5-methylisatin, 2188 acyl Pictet-Spengler reaction, 2210 5-oxazolone, 353 acyl transfer reaction, 168 5-sulfamoylisatin, 2188 acylbenzenesulfonylhydrazide, 1853 5,5-dimethylhydantoin, 1835 acyloin, 13, 14, 18,493,833,1317,1319 10 5,6-dimethoxy-l-indanone, 1128 acyloxyheteroarene, 1143 1 6-endo-dig radical cyclization, 1167 AD-mix-a, 2574, 2577 lyl)-4­ 6-oxadihydrouracil, 1408 AD-mix-,B, 2574, 2575, 2576 ride, 14, 1938, 8-hydroxquinaldine, 374, 375 Adams catalyst, 2780 9-bromomethylanthracene, 3070 additive Pummerer reaction, 2285 9-formylellipticine,724 additive seleno Pummerer rearrangement, 2286 9-methylanthracene, 3070 adipic acid, 364,1096,1097,1948,3116 1531 9-phenylfluorene, 1379 ADMET, 57, 58 n,537 aerosol, 766 absolute configuration, 1021, 1983, 1984, 1985 aglycon, 1046, 1408, 1410,1650,1843 2,2023 acenaphthylene, 820 aglycone, 1650, 2983 ~75 acetamidine, 2241 alcoholysis, 669, 677, 1473, 1872,2911 acetanilide, 1569,2092,2201 aldimine stannichloride, 2659 acetoacetic ester, 9, 25 aldimine,74, 1491, 1821,2660,2770 19 acetoacetone,688, 1038, 1422,1633,3130 alditol, 2718 3634 SUBJECT INDEX aldoketene, 822 allenic Pauson-Khand reaction, 2132 aldol reaction, 45,858,1022, 1187,1299, 1305, allenylation, 1779 1383,1508,1606,2523,2697,2783,2785 allenylsilane, 837 aldol-Tishchenko reaction, 2783, 2784 allocyathin, 1367 aldonamide, 2946 allyl furohydroximate, 3045 aldonic acid, 2446 allyl sulfenate, 1952 aldononitrile, 3056, 3057 allyl sulfoxide, 1064, 1952 aldose, 74, 75,1403,1404,1613,1614, 1763, allyl tri-n-butylstannane, 1597 2400,2446,2852,3056,3057 allylation, 1187, 1491, 1492, 1777, 1778, 1779, aldoxime, 376, 2017 2799,2812,2813 aleuritic acid, 2865 allylethylamine, 147 a1foI1214,3134 allylic oxidation, 2395, 2396, 2476 alfol 6, 3134 allylsilane, 683, 837, 1103, 1491, 1803 alfol 8, 3134 allylstannane, 837, 2679 aliphatic S-N Smiles rearrangement, 2611 allyltriisopropylsilane, 837 Alizarin Bordeaux, 461 allyltrimethylsilane, 1491, 1492,1493,2373 Alizarin Cyanin Black, 461 altohyrtin A, 1021, 1288 Alizarin Cyanine R, 461 aluminum isopropylate, 1288 Alizarin Green S, 461 amberlite 1R-120, 2949 alkenylsilane, 3100 amberlite IR-4B, 1622 alkoxy ethylenimine, 2018 amberlite IRA-4oo, 1622 alkoxy radical fragmentation (ARF), 2718 amentoflavone, 2983 alkoxyketene, 308 amidation, 25, 2399, 3186 alkoxyphosphorane, 1955 amidine, 288,2233,2234,2239, 2241,2243, alkoxysilane, 3146 2294 alkoxysulfane, 1929 amidoalkylation, 1443,2808 alkyl dinitrone, 2221 amidoxime, 2773 alkyl imidate, 1713 amidrazone, 2242 alkyl phthalimidoacetate, 1183 aminal, 1069 alkyl selenoxide, 2548 amination,315,544, 554, 1009, 1358, 1359, alkyl sulfonate, 2707, 2708 1360,1569,1737,2303,2771,2799 alkylaniline,924, 1194 aminoalcohol, 1222, 1384, 1808,2779 alkylation, 9, 181,215,411,416,863,930, aminohydroxylation, 2568, 2569, 2570 939,974,978,993,1001,1036,1120,1131, aminoketene, 308 1132,1176,1314,1342,1418,1469,1811, aminolactol, 3032 1913,1930,1955,1983,2164,2290,2303, aminolysis, 353,445, 1222 2336,2523,2695,2697,2799,2807,2998, aminophenol, 191,498,499, 1622, 1745,2198, 3004,3027,3190 3186 alkylative decarboxylation, 1687 aminopolysaccharide, 75 alkylidenation, 1170, 1171 arninopyridine,631,693,753,921,2890,2891 alkylidene metallacycie mechanism, 3150 aminopyrimidine,497, 1408, 1410,2789,2890 alkylidene, 353,1321,2892,3148 aminostyrene, 142, 1165, 1358,3008 a1kylidenecyciopropane, 515, 516 aminotetrahydroquinoline, 1640 alkylnitrite, 1867,2868 aminotriazole, 2159 alkylphosphonic acid, 669 amozonolysis, 766 alkylsulfonamide, 946 amphidinolide A, 2680 alkynedicobalt hexacarbonyl complex, 2131 amphidinolide B I, 1021 alkynide, 717 amphotericin B, 1485 alkynolate anion, 1683 amyl nitrite, 1627, 1629 alkynone, 2963 androgen, 2988 allene, 536,808, 819, 821, 822,828,837,930, androgenic assay, 3158 1274,1719,2003,2132,2548 androsterone, 3160 SUBJECT INDEX 3635 ldreaction, 2132 angucycline, 507 arabinose, 1614, 1615, 1789,2446,2448,2852, anhalonidine methiodide, 991 2949,3056,3059 anil, 923, 1137,2385,2604,2673 arene, 1170,1496, 1861, 1862,1866,2049, anilide, 1144, 1638 3184 :e,3045 aniline, 116, 117, 142, 192,377,406,408,447, arenesulfinate, 1131 499,577,688,921,922,924,925,942,947, arenesulfonamide, 1418 , 1952 948, 1041, 1069,1080, 1140, 1165, 1193, arenesulfonate, 1131 ane, 1597 1194,1198,1252,1314,1359,1415,1418, argentic oxide, 723 1,1492,1777,1778,1779, 1458,1471,1554,1569,1572,1628,1629, aromatic diazonium tetrafluoroborate, 1248 1638,1717,2093,2245,2326,2328,2385, aromaticity, 848, 897, 1131, 1883,2514,2622, 2386,2387,2455,2504,2626,2651,2722, 2927,3009,3082,3179,3188 15,2396,2476 2726,3019,3060,3061,3062,3065,3066, aromatization, 900, 1345, 1477, 1504,2553, 1103,1491,1803 3130,3172 2892,2912 679
Recommended publications
  • 14.8 Organic Synthesis Using Alkynes
    14_BRCLoudon_pgs4-2.qxd 11/26/08 9:04 AM Page 666 666 CHAPTER 14 • THE CHEMISTRY OF ALKYNES The reaction of acetylenic anions with alkyl halides or sulfonates is important because it is another method of carbon–carbon bond formation. Let’s review the methods covered so far: 1. cyclopropane formation by the addition of carbenes to alkenes (Sec. 9.8) 2. reaction of Grignard reagents with ethylene oxide and lithium organocuprate reagents with epoxides (Sec. 11.4C) 3. reaction of acetylenic anions with alkyl halides or sulfonates (this section) PROBLEMS 14.18 Give the structures of the products in each of the following reactions. (a) ' _ CH3CC Na| CH3CH2 I 3 + L (b) ' _ butyl tosylate Ph C C Na| + L 3 H3O| (c) CH3C' C MgBr ethylene oxide (d) L '+ Br(CH2)5Br HC C_ Na|(excess) + 3 14.19 Explain why graduate student Choke Fumely, in attempting to synthesize 4,4-dimethyl-2- pentyne using the reaction of H3C C'C_ Na| with tert-butyl bromide, obtained none of the desired product. L 3 14.20 Propose a synthesis of 4,4-dimethyl-2-pentyne (the compound in Problem 14.19) from an alkyl halide and an alkyne. 14.21 Outline two different preparations of 2-pentyne that involve an alkyne and an alkyl halide. 14.22 Propose another pair of reactants that could be used to prepare 2-heptyne (the product in Eq. 14.28). 14.8 ORGANIC SYNTHESIS USING ALKYNES Let’s tie together what we’ve learned about alkyne reactions and organic synthesis. The solu- tion to Study Problem 14.2 requires all of the fundamental operations of organic synthesis: the formation of carbon–carbon bonds, the transformation of functional groups, and the establish- ment of stereochemistry (Sec.
    [Show full text]
  • Handbook of Less-Common Nanostructures
    HANDBOOK OF LESS-COMMON NANOSTRUCTURES Boris I. Kharisov • Oxana Vasilievna Kharissova Ubaldo Ortiz-Mendez CRC Press Taylor &. Francis Croup Boca Raton London NewYork CRC Press is an imprint of the Taylor & Francis Group, an Informa business Contents Abbreviations xix Preface xxiii Acknowledgments xxv Authors xxvii PART I Introduction to Nanostructures Chapter 1 Methods for Obtaining Nanoparticles and Other Nanostructures 3 1.1 General Remarks on Nanoparticle Fabrication 3 1.2 Examples of Several Important Methods for the Synthesis of Nanoobjects 3 1.2.1 Vapor and Plasma-Based Techniques 3 1.2.2 Electrochemical Methods 10 1.2.3 Microwave, Ultrasonic, and UV-Irradiation Techniques 14 1.2.4 High-Pressure Methods 18 1.2.5 Use of Microfluidic Chips 20 1.2.6 Synthesis in Reversed Micelles 21 1.2.7 Hot-Plate Method 21 1.2.8 Other Chemical Routes 22 1.2.9 Biochemical and Self-Assembly Methods 24 1.3 "Green" Aspects of Nanoparticle Synthesis 26 References 27 Chapter 2 Brief Description of Some Classic Nanostructures 31 2.1 Carbon-Based Nanostructures 31 2.1.1 Carbon Nanotubes 31 2.1.2 Fullerenes 34 2.1.3 Nanodiamonds 35 2.1.4 Graphene and Graphane 37 2.2 Conventional Noncarbon Nanostructures 38 2.2.1 Simple and Core-Shell Nanoparticles 38 2.2.2 Nanometals 42 2.2.3 Gallery of Other Conventional Nanostructures 42 References 48 PART II Less-Common Nanostructures Chapter 3 Simple, Linear ID, 2D, and 3D Nanostructures 57 3.1 Nanolines 57 3.2 Nanopencils 61 ix X Contents 3.3 Nanodumbbells 66 3.4 Nanoshuttles 70 3.5 Nanopeapods 73 3.6 Nanopins 77 3.7
    [Show full text]
  • S1 Supporting Information Copper-Catalyzed
    Supporting Information Copper-Catalyzed Semihydrogenation of Internal Alkynes with Molecular Hydrogen Takamichi Wakamatsu, Kazunori Nagao, Hirohisa Ohmiya*, and Masaya Sawamura* Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan Table of Contents Instrumentation and Chemicals S1 Characterization Data for Alkynes S1–S2 Procedure for the Copper-Catalyzed Semihydrogenation of Alkynes S2 Characterization Data for Alkenes S3–S5 References S5 NMR Spectra S6–S31 Instrumentation and Chemicals NMR spectra were recorded on a JEOL ECX-400, operating at 400 MHz for 1H NMR and 100.5 13 1 13 MHz for C NMR. Chemical shift values for H and C are referenced to Me4Si and the residual solvent resonances, respectively. Mass spectra were obtained with Thermo Fisher Scientific Exactive, JEOL JMS-T100LP or JEOL JMS-700TZ at the Instrumental Analysis Division, Equipment Management Center, Creative Research Institution, Hokkaido University. TLC analyses were performed on commercial glass plates bearing 0.25-mm layer of Merck Silica gel 60F254. Silica gel (Kanto Chemical Co., Silica gel 60 N, spherical, neutral) was used for column chromatography. Materials were obtained from commercial suppliers or prepared according to standard procedure unless otherwise noted. CuCl was purchased from Aldrich Chemical Co., stored under nitrogen, and used as it is. NatOBu, octane and 6-dodecyne 1a were purchased from TCI Chemical Co., stored under nitrogen, and used as it is. Diphenylacetylene 1j was purchased from Wako Chemical Co., stored under nitrogen, and used as it is. 1,4-Dioxane was purchased from Kanto Chemical Co., distilled from sodium/benzophenone and stored over 4Å molecular sieves under nitrogen.
    [Show full text]
  • 779 Part 770—Interpretations
    Pt. 770 15 CFR Ch. VII (1–1–21 Edition) in the item that qualitatively affect the per- roller bearings and parts). This applies formance of the U.S. and foreign items; to separate shipments of anti-friction (vi) Evidence of the interchangeability of bearings or bearing systems and anti- U.S. and foreign items; friction bearings or bearing systems (vii) Patent descriptions for the U.S. and foreign items; shipped with machinery or equipment (viii) Evidence that the U.S. and foreign for which they are intended to be used items meet a published industry, national, or as spares or replacement parts. international standard; (2) An anti-friction bearing or bear- (ix) A report or eyewitness account, by ing system physically incorporated in a deposition or otherwise, of the foreign item’s segment of a machine or in a complete operation; machine prior to shipment loses its (x) Evidence concerning the foreign manu- identity as a bearing. In this scenario, facturers’ corporate reputation; (xi) Comparison of the U.S. and foreign end the machine or segment of machinery item(s) made from a specific commodity, containing the bearing is the item sub- tool(s), device(s), or technical data; or ject to export control requirements. (xii) Evidence of the reputation of the for- (3) An anti-friction bearing or bear- eign item including, if possible, information ing system not incorporated in a seg- on maintenance, repair, performance, and ment of a machine prior to shipment, other pertinent factors. but shipped as a component of a com- plete unassembled (knocked-down) ma- SUPPLEMENT NO.
    [Show full text]
  • The Synthesis of a Polydiacetylene to Create a Novel Sensory Material
    SELDE, KRISTEN A., M.S. The Synthesis of a Polydiacetylene to Create a Novel Sensory Material. (2007) Directed by Dr. Darrell Spells. 47pp. Sensory materials that respond to chemical and mechanical stimuli are under development in many laboratories. There are many significant uses of polydiacetylene compounds as sensory material. They have been applied to drug delivery, drug design, biomolecule development, cosmetics, and national security. In this study, experiments were carried out toward the development of a novel sensory material based on the established synthetic research on polydiacetylene compounds. Synthetic routes toward sensory materials with different head groups, different carbon chains lengths, and the incorporation of molecular imprints were explored. Diacetylene moieties, which can be used for polymer vesicle formation, were prepared by two main routes. In one route, 1-iodo-1-octyne and 1-iodo-1-dodecyne were prepared as starting materials for the synthesis of two diacetylene compounds (Diacetylene I and Diacetylene II). In the other route, a mesityl alkyne was used to prepare 5-iodo-1-pentyne, which was then used to prepare a triethylamino alkyne. This in turn was used to synthesize a diacetylene (Diacetylene III). Although each diacetylene product was formed, purification by column chromatography was found to be difficult. Experiments in vesicle formation, with and without molecular imprints, were also carried out using commercially available diacetylenes . THE SYNTHESIS OF A POLYDIACETYLENE TO CREATE A NOVEL SENSORY
    [Show full text]
  • Synthesis, Reactivity, and Catalysis of Group 3 and Lanthanide Alkyl Complexes
    Synthesis, Reactivity, and Catalysis of Group 3 and Lanthanide Alkyl Complexes By Daniel Steven Levine A dissertation submitted in partial satisfaction of the requirements for the degree of Doctor of Philosophy in Chemistry in the Graduate Division of the University of California, Berkeley Committee in charge: Professor T. Don Tilley, Co-Chair Professor Richard A. Andersen, Co-Chair Professor Alexis T. Bell Summer 2016 Abstract Synthesis, Reactivity, and Catalysis of Group 3 and Lanthanide Alkyl Complexes by Daniel Steven Levine Doctor of Philosophy in Chemistry University of California, Berkeley Professor T. Don Tilley, Co-Chair Professor Richard A. Andersen, Co-Chair Chapter 1. A series of scandium dialkyl complexes, (PNP)ScR2 (R = neopentyl, trimethylsilylmethyl), supported by the monoanionic, chelating PNP ligand (2,5- bis(dialkylphosphinomethyl)pyrrolide; alkyl = cyclohexyl, tert-butyl) was synthesized and the reactivities of these complexes toward simple hydrocarbons was investigated. The scandium– carbon bonds undergo σ-bond metathesis reactions with hydrogen and these complexes are catalysts for the hydrogenation of alkenes. Reactions with primary amines led to formation of amido complexes that undergo cyclometalation via σ-bond metathesis, without involvement of an imido complex intermediate. A variety of carbon-hydrogen bonds are also activated, including sp-, sp2-, and sp3-C–H bonds (intramolecularly in the latter case). Levine, D. S.; Tilley, T. D.; Andersen, R. A. Organometallics 2015, 34 (19), 4647. Chapter 2. Terminal group 3 methylidene complexes are generated by thermolysis of monoanionic PNP-supported scandium and yttrium dialkyl complexes. The reaction mechanism has been probed by deuterium-labeling experiments and DFT calculations. Abstraction of a γ- hydrogen from one alkyl group by the other affords a metallacyclobutane that undergoes [2+2] cycloreversion, analogous to a key step in the olefin metathesis reaction, to generate a methylidene complex and isobutene.
    [Show full text]
  • Development of a Solid-Supported Glaser-Hay Reaction and Utilization in Conjunction with Unnatural Amino Acids
    W&M ScholarWorks Dissertations, Theses, and Masters Projects Theses, Dissertations, & Master Projects 2015 Development of a Solid-Supported Glaser-Hay Reaction and Utilization in Conjunction with Unnatural Amino Acids Jessica S. Lampkowski College of William & Mary - Arts & Sciences Follow this and additional works at: https://scholarworks.wm.edu/etd Part of the Organic Chemistry Commons Recommended Citation Lampkowski, Jessica S., "Development of a Solid-Supported Glaser-Hay Reaction and Utilization in Conjunction with Unnatural Amino Acids" (2015). Dissertations, Theses, and Masters Projects. Paper 1539626985. https://dx.doi.org/doi:10.21220/s2-r9jh-9635 This Thesis is brought to you for free and open access by the Theses, Dissertations, & Master Projects at W&M ScholarWorks. It has been accepted for inclusion in Dissertations, Theses, and Masters Projects by an authorized administrator of W&M ScholarWorks. For more information, please contact [email protected]. Development of a Solid-Supported Glaser-Hay Reaction and Utilization in Conjunction with Unnatural Amino Acids Jessica Susan Lampkowski Ida, Michigan B.S. Chemistry, Siena Heights University, 2013 A Thesis presented to the Graduate Faculty of the College of William and Mary in Candidacy for the Degree of Master of Science Chemistry Department The College of William and Mary May, 2015 COMPLIANCE PAGE Research approved by Institutional Biosafety Committee Protocol number: BC-2012-09-13-8113-dyoung01 Date(s) of approval: This protocol will expire on 2015-11-02 APPROVAL PAGE This
    [Show full text]
  • Transition Metal-Catalyzed Directed C(Sp3)–H Functionalization of Saturated Heterocycles
    Synthesis Review / Short Review Transition Metal-Catalyzed Directed C(sp3)–H Functionalization of Saturated Heterocycles Daniele Antermitea James A. Bull*a a Department of Chemistry, Imperial College London, White City, Wood Lane, London, W12 0BZ, United Kingdom [email protected] Click here to insert a dedication. Received: biological interactions or selectivity profiles. The ready Accepted: Published online: availability of simple saturated heterocycle derivatives, DOI: including enantioenriched derivatives, makes them ideal Abstract Synthetic methods that can readily access saturated heterocycles starting points for further reactions. Therefore, approaches to with different substitution patterns and with control of stereo- and functionalize existing C–H bonds of these readily available regiochemistry are of huge potential value in the development of new medicinal compounds. Directed C–H functionalization of simple and building blocks appears to be of considerable potential. commercially available precursors offers the potential to prepare diverse Over the last 20 years, the concept of transition metal- collections of such valuable compounds that can probe the different available exit vectors from a ring system. Nonetheless, the presence of the catalyzed C–H functionalization has emerged with enormous Lewis basic heteroatoms makes this a significant challenge. This review potential to streamline the synthesis of complex molecules.5 covers recent advances in the catalytic C–H functionalization of saturated Specifically, transition metal catalysts can activate C–H bonds heterocycles, with a view to different heterocycles (N, O, S), substitution to form discrete C–M bonds, via different mechanistic patterns and transformations. 1. Introduction pathways.6 The resulting organometallic intermediate can then 2 a-C–H Functionalization with directing group on nitrogen form new C–C or C–heteroatom bonds with various coupling 3 C–H Functionalization at unactivated C(3), C(4) and C(5) positions partners.
    [Show full text]
  • Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides
    Top Curr Chem (Z) (2016) 374:16 DOI 10.1007/s41061-016-0016-4 REVIEW Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides 1 1 Jan Dommerholt • Floris P. J. T. Rutjes • Floris L. van Delft2 Received: 24 November 2015 / Accepted: 17 February 2016 / Published online: 22 March 2016 Ó The Author(s) 2016. This article is published with open access at Springerlink.com Abstract A nearly forgotten reaction discovered more than 60 years ago—the cycloaddition of a cyclic alkyne and an organic azide, leading to an aromatic triazole—enjoys a remarkable popularity. Originally discovered out of pure chemical curiosity, and dusted off early this century as an efficient and clean bio- conjugation tool, the usefulness of cyclooctyne–azide cycloaddition is now adopted in a wide range of fields of chemical science and beyond. Its ease of operation, broad solvent compatibility, 100 % atom efficiency, and the high stability of the resulting triazole product, just to name a few aspects, have catapulted this so-called strain-promoted azide–alkyne cycloaddition (SPAAC) right into the top-shelf of the toolbox of chemical biologists, material scientists, biotechnologists, medicinal chemists, and more. In this chapter, a brief historic overview of cycloalkynes is provided first, along with the main synthetic strategies to prepare cycloalkynes and their chemical reactivities. Core aspects of the strain-promoted reaction of cycloalkynes with azides are covered, as well as tools to achieve further reaction acceleration by means of modulation of cycloalkyne structure, nature of azide, and choice of solvent. Keywords Strain-promoted cycloaddition Á Cyclooctyne Á BCN Á DIBAC Á Azide This article is part of the Topical Collection ‘‘Cycloadditions in Bioorthogonal Chemistry’’; edited by Milan Vrabel, Thomas Carell & Floris P.
    [Show full text]
  • A. Discovery of Novel Reactivity Under the Sonogashira Reaction Conditions B. Synthesis of Functionalized Bodipys and BODIPY-Sug
    A. Discovery of novel reactivity under the Sonogashira reaction conditions B. Synthesis of functionalized BODIPYs and BODIPY-sugar conjugates Ravi Shekar Yalagala, M.Phil Department of Chemistry Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy Faculty of Mathematics and Science, Brock University St. Catharines, Ontario © 2016 ABSTRACT A. During our attempts to synthesize substituted enediynes, coupling reactions between terminal alkynes and 1,2-cis-dihaloalkenes under the Sonogashira reaction conditions failed to give the corresponding substituted enediynes. Under these conditions, terminal alkynes underwent self-trimerization or tetramerization. In an alternative approach to access substituted enediynes, treatment of alkynes with trisubstituted (Z)- bromoalkenyl-pinacolboronates under Sonogashira coupling conditions was found to give 1,2,4,6-tetrasubstituted benzenes instead of Sonogashira coupled product. The reaction conditions and substrate scopes for these two new reactions were investigated. B. BODIPY core was functionalized with various functional groups such as nitromethyl, nitro, hydroxymethyl, carboxaldehyde by treating 4,4-difluoro-1,3,5,7,8- pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene with copper (II) nitrate trihydrate under different conditions. Further, BODIPY derivatives with alkyne and azido functional groups were synthesized and conjugated to various glycosides by the Click reaction under the microwave conditions. One of the BODIPY–glycan conjugate was found to form liposome upon rehydration. The photochemical properties of BODIPY in these liposomes were characterized by fluorescent confocal microscopy. ii ACKNOWLEDGEMENTS I am extremely grateful to a number of people. Without their help, this document would have never been completed. First and foremost, I would like to thank my supervisor and mentor Professor Tony Yan for his guidance and supervision to make the thesis possible.
    [Show full text]
  • Indolizidines and Quinolizidines: Natural Products and Beyond
    Indolizidines and quinolizidines: natural products and beyond Edited by Joseph Philip Michael Generated on 05 October 2021, 08:24 Imprint Beilstein Journal of Organic Chemistry www.bjoc.org ISSN 1860-5397 Email: [email protected] The Beilstein Journal of Organic Chemistry is published by the Beilstein-Institut zur Förderung der Chemischen Wissenschaften. This thematic issue, published in the Beilstein Beilstein-Institut zur Förderung der Journal of Organic Chemistry, is copyright the Chemischen Wissenschaften Beilstein-Institut zur Förderung der Chemischen Trakehner Straße 7–9 Wissenschaften. The copyright of the individual 60487 Frankfurt am Main articles in this document is the property of their Germany respective authors, subject to a Creative www.beilstein-institut.de Commons Attribution (CC-BY) license. Indolizidines and quinolizidines: natural products and beyond Joseph P. Michael Editorial Open Access Address: Beilstein Journal of Organic Chemistry 2007, 3, No. 27. Molecular Sciences Institute, School of Chemistry, University of the doi:10.1186/1860-5397-3-27 Witwatersrand, PO Wits 2050, South Africa Received: 24 September 2007 Email: Accepted: 26 September 2007 Joseph P. Michael - [email protected] Published: 26 September 2007 © 2007 Michael; licensee Beilstein-Institut. License and terms: see end of document. Alkaloids occur in such astonishing profusion in nature that amphibians. [5,6] It is thus hardly surprising that both the struc- one tends to forget that they are assembled from a relatively tural elucidation and the total synthesis of these and related small number of structural motifs. Among the motifs that are alkaloids continue to attract the attention of eminent chemists, most frequently encountered are bicyclic systems containing as borne out by the seemingly inexhaustible flow of publica- bridgehead nitrogen, especially 1-azabicyclo[4.3.0]nonanes and tions in prominent journals.
    [Show full text]
  • Organic Materials for Electronic Devices
    Organic Materials for Electronic Devices by Lichang Zeng Submitted in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy Supervised by Professor Shaw H. Chen and Professor Ching W. Tang Department of Chemical Engineering Arts, Sciences and Engineering Edmund A. Hajim School of Engineering and Applied Sciences University of Rochester Rochester, New York 2010 ii To my family iii CURRICULUM VITAE Lichang Zeng was born in 1978 in Fujian, China. In 2001, he received a Bachelors of Engineering degree in Polymer Materials from Zhejiang University, Hangzhou, China. He continued on at Zhejiang University receiving his Master of Science degree in 2004. He then moved to the University of Rochester to pursue his doctorate in Chemical Engineering under the joint supervision of Professors Shaw H. Chen and Ching W. Tang, receiving a Master of Science degree in 2009. His field of research was in organic electronic materials and devices. Selected Publications in Referee Journals 1. Zeng, L. C.; Tang, C. W.; Chen, S. H. “Effects of Active Layer Thickness and Thermal Annealing on Polythiophene:Fullerene Bulk Heterojunction Photovoltaic Cells.” Applied Physics Letters, 2010, 97, 053305. 2. Zeng, L. C.; Blanton, T. N.; Chen, S. H. “Modulation of Phase Separation between Spherical and Rod-Like Molecules Using Geometric Surfactancy.” Langmuir 2010, 26, 12877. 3. Zeng, L. C.; Lee, T. Y. S.; Merkel, P. B.; Chen, S. H. “A New Class of Non-Conjugated Bipolar Hybrid Hosts for Phosphorescent Organic Light-Emitting Diodes.” Journal of Materials Chemistry 2009, 19, 8772. 4. Zeng, L. C.; Yan, F.; Wei, S. K. H.; Culligan, S.
    [Show full text]