Macrocyclic Polyether Syntheses

Автор(ы):Gokel G. W., Korzeniowski S. H.
06.10.2007
Год изд.:1982
Описание: It seems likely that no project of this magnitude is undertaken in the absence of several motivations. This book is no exception. There are at least two rational reasons for conducting this cataloging and organizational effort. The first of these is the obvious fact that a very large number of macrocyclic polyethers have now been prepared and nowhere is there a comprehensive listing of them. A number of excellent reviews have been published dealing with one or more aspects of macrocycle chemistry, but the authors felt a great need for a single source listing known compounds. They have, therefore, attempted to provide such a listing to assist ourselves in keeping track as well as, they hope, helping others in this field.
Оглавление:
Macrocyclic Polyether Syntheses — обложка книги.
Chapter 1. Introduction and General Principles [1]
  1.1 Background [1]
  1.2 Pedersen's Discovery of Crown Compounds [1]
  1.3 Nomenclature and Jargon [2]
    1.3.1 Crown Ether [2]
    1.3.2 Azacrown [4]
    1.3.3 In-Out Bicyclic Amines [4]
    1.3.4 Cryptands and Cryptate Complexes [4]
    1.3.5 Lariat Ethers [6]
    1.3.6 Crown Esters [6]
    1.3.7 Spherands [6]
    1.3.8 Cascades [7]
    1.3.9 Polypodes and Octopus Molecules [7]
    1.3.10 Host-Guest-Chemistry [7]
    1.3.11 Conventions [8]
  1.4 The Cycloohgomenzation of Ethylene Oxide [8]
  1.5 Polyazamacrocycles as Complexmg Agents for Transition Metals [10]
  1.6 References [10]
Chapter 2. The Template Effect [12]
  2.1 Introduction [12]
  2.2 Operation of the Template Effect [12]
  2.3 Evidence for the Template Effect [13]
  2.4 Complexation Constants and the Template Effect [18]
  2.5 References [18]
Chapter 3. Syntheses of Oxygen Macrocycles [19]
  3.1 Pedersen's First Crowns [19]
  3.2 Syntheses of 18-Crown-6 [21]
  3.3 Syntheses of Dibenzo and Dicyclohexano-18-Crown-6 [23]
  3.4 Synthesis of Substituted Benzocrowns [26]
  3.5 Crowns Incorporating the Xylylene Unit [28]
  3.6 Furan-containing Macrocycles [31]
  3.7 Crowns Containing the Paracyclophanyl Unit [34]
  3.8 Bis-Crowns [34]
  3.9 Lariat Ethers [39]
  3.10 Miscellaneous Crown Systems [40]
  3.11 Newkome's Pyridine-containing Macrocycles [44]
  3.12 Okahara's One-pot Approach [46]
  3.13 Chiral Crowns [47]
    3.13.1 Cram's Chiral Binaphthyl Systems [47]
    3.13.2 Crowns Incorporating the Tartaric or Lactic Acid Subunit [50]
    3.13.3 Crowns Incorporating Sugar Subunits [52]
  3.14. Organometallic Derivatives of Crowns [53]
  3.15 Cesium Salts in Crown Synthesis [53]
  3.16 Listings of Tables [54]
  3.17 Tables 3.1-3.29 [55]
  3.18 References [150]
Chapter 4. Syntheses of Azacrowns [156]
  4.1 Introduction [156]
  4.2 Monoazacrowns [156]
  4.3 Bridged Monoazacrowns [159]
  4.4 Diazacrowns [160]
  4.5 Cyclams [162]
  4.6 Cyclic Oximes [164]
  4.7 Macrocyclic Imines [164]
  4.8 Thioazamacrocycles [165]
  4.9 Biologically Active Azacrowns [165]
  4.10 Crown Ether Based Dyes [166]
  4.11 Newkome's Pyridine-containing Macrocycles [167]
  4.12 Listing of Tables [167]
  4.13 Tables 4.1-4.21 [168]
  4.14 References [216]
Chapter 5. Crown Esters and Macrocyclic Polyether Lactones [220]
  5.1 Introduction [220]
  5.2 General Ester Synthesis [220]
  5.3 Macrocyclic Ester Properties [222]
  5.4 One-pot Macrocyclic Lactone Synthesis [222]
  5.5 The Hantzsch Condensation [223]
  5.6 Antibiotic Models [224]
  5.7 Stannoxanes as Covalent Templates [225]
  5.8 Macrocyclic Esters by Ozonolysis [225]
  5.9 Photochemical Macrocyclization [225]
  5.10 Listing of Tables [226]
  5.11 Tables 5.1-5.14 [227]
  5.12 References [264]
Chapter 6. Miscellaneous Macrocycles [267]
  6.1 Macrocyclic Polyether Acetals [267]
  6.2 Macrocyclic Thioethers [268]
    6.2.1 Simple Sulfur Macrocycles [268]
    6.2.2 Macrocycles with Sulfur-containing Subunits [269]
    6.2.3 Macrocyclic Polysulfides [270]
  6.3 Mixed Sulfur-Nitrogen Macrocycles [271]
  6.4 Phosphorus and Arsenic-containing Macrocycles [273]
  6.5 Silicon-containing Macrocycles [275]
  6.6 Polymer-bound Macrocycles [276]
    6.6.1 Pendant Crown Polymers [276]
    6.6.2 Crown Ether Copolymers [278]
    6.6.3 Polycrowns [279]
    6.6.4 Pseudocrowns [279]
  6.7 Listing of Tables [280]
  6.8 Tables 6.1-6.4 [280]
  6.9 References [308]
Chapter 7. Open-chained Equivalents of Crown Ethers [311]
  7.1 Introduction [311]
  7.2 Uses of Open-chained Equivalents in PTC [312]
  7.3 Octopus Molecules [314]
  7.4 Substituted Podands [316]
  7.5 Synthetic lonophores [317]
  7.6 Listing of Tables [319]
  7.7 Tables 7.1-7.13 [320]
  7.8 References [345]
Chapter 8. Cryptands and Related Polycyclic Systems [347]
  8.1 Inception and General Syntheses [347]
  8.2 Cryptands Containing Sulfur and Nitrogen in the Bridges [349]
  8.3 Lipophilic Cryptands [351]
  8.4 Cryptands Containing a Carbon Bridgehead [352]
  8.5 Chiral Cryptands [354]
  8.6 Miscellaneous Cryptands [355]
  8.7 Macropolycyclic Cryptands [356]
  8.8 Polymer-bound Cryptands [357]
  8.9 Listing of Tables [358]
  8.10 Tables 8.1-8.5 [359]
  8.11 References [393]
Author Index [395]
Subject Index [405]

Chapter 3. Tables
  3.1 Derivatives of 12-crown-4 [55]
  3.2 Derivatives of 15-crown-5 [58]
  3.3 Derivatives of 18-crown-6 [61]
  3.4 Crowns containing fused cyclohexano subunits [69]
  3.5 Miscellaneous alicyclic crowns [71]
  3.6 Crowns containing a ketonic carbonyl as part of the macroring [76]
  3.7 Benzo-15-crown-5 derivatives [77]
  3.8 Derivatives of monobenzo-18-crown-6 [81]
  3.9 Derivatives of dibenzo-18-crown-6 [94]
  3.10 Miscellaneous dibenzo crowns [101]
  3.11 Crowns containing two or more fused benzo units [105]
  3.12 Crowns having on ortho-xylyl subunit as part of the macroring [107]
  3.13 Miscellaneous fused ortho-benzo crowns [108]
  3.14 Crowns having a meta-xylyl subunit as part of the macroring [109]
  3.15 Crowns having a meta-benzo unit as part of the macroring [111]
  3.16 Crowns having a para-benzo subunit as part of the macroring [112]
  3.17 Miscellaneous crowns containing the biphenyl subunit [113]
  3.18 Crowns containing the naphthalene subunit as part of the macroring [114]
  3.19 Crown compounds containing a single 2,2'-binaphthyl subunit [116]
  3.20 Crown compounds containing two 2,2'-binaphthyl subunits [125]
  3.21 Crowns containing miscellaneous aromatics as part of the macroring [130]
  3.22 Crown compounds having a spiro-3,3-oxetane subunit in the macroring [132]
  3.23 Crown compounds containing the furan subunit [133]
  3.24 Crowns containing a 3,4-thienyl subunit [140]
  3.25 Crowns containing the 4,6-pynmidine subunit [140]
  3.26 Crown compounds containing pyndyl or bipyridyl subunits [141]
  3.27 Crown compounds containing two macrocyclic rings [141]
  3.28 Macrocyclic oligomers (see also Table 6.4) [147]
  3.29 Polymeric crowns (see also Table 6.4) [149]
Chapter 4. Tables
  4.1 Monoazacrowns [168]
  4.2 Diazacrowns containing secondary nitrogen [169]
  4.3 Diaza-18-crowns containing tertiary nitrogen [172]
  4.4 Diazacrowns containing tertiary nitrogens [176]
  4.5 Azacrowns containing two substituted nitrogens [180]
  4.6 Azacrowns containing more than two substituted nitrogens [182]
  4.7 All-nitrogen crowns having the nitrogens predominantly unsubstituted [184]
  4.8 All-nitrogen crowns having the nitrogens predominantly substituted [187]
  4.9 Nitrogen crowns containing amide functions [189]
  4.10 Miscellaneous benzocrowns containing nitrogen [190]
  4.11 Monoazacrowns containing a 4-substituted phenyl on nitrogen [191]
  4.12 Azacrowns containing the 3,3-bis(methyleneoxy)oxetane subunit [194]
  4.13 Azacrowns containing the furan subunit [194]
  4.14 Azacrowns containing the pyridine-1,6-diheteroatom subunit [196]
  4.15 Azacrowns containing the 2,6-picolinoly subunit [199]
  4.16 Azacrowns containing the pyridine-2,6-dimethylene subunit [201]
  4.17 Azacrowns containing the benzene-1,3-bis-(aminomethylene) subunit [208]
  4.18 Azacrowns containing the 1,3-pyridazine or 1,3,5-triazine subunit [209]
  4.19 Azacrowns containing the 2,2'-bipyridyl subunit [211]
  4.20 Azacrowns containing two or more macrorings [212]
  4.21 Miscellaneous azacrowns [214]
Chapter 5. Tables
  5.1 Macrocyclic oxalate esters [227]
  5.2 Macrocyclic malonate esters [228]
  5.3 Macrocyclic butanoate and butenoate esters [229]
  5.4 Macrocyclic diglycolate esters [231]
  5.5 Macrocyclic thiodiglycolate esters [232]
  5.6 Macrocyclic phthalate esters [234]
  5.7 Macrocyclic isophthalate esters [237]
  5.8 Macrocyclic terephthalate esters [233]
  5.9 Macrocyclic esters of furan-2,5-dicarboxylic acid [240]
  5.10 Macrocyclic amides and esters containing the 2,6-dipicolinate subunit [241]
  5.11 Macrocyclic esters containing the 3,5-dipicolinate subunit [245]
  5.12 Macrocyclic diphenyldisulfides [248]
  5.13 Miscellaneous mono- and diesters [249]
  5.14 Miscellaneous lactams, cyclic carbamates, carbonates, ureas, etc [254]
Chapter 6. Tables
  6.1 Macrocyclic acetals and thioacetals [280]
  6.2 Macrocycles containing phosphorus or arsenic [282]
  6.3 Macrocycles containing one or more sulfur atoms [285]
  6.4 Crown-containing polymers and polycrowns (see also Tables 3.28] and 3.29) [304]
Chapter 7. Tables
  7.1 Simple ethers [320]
  7.2 Open-chained systems containing the disubstituted benzene subunit [321]
  7.3 Open-chained ligands having atomatic terminal groups [323]
  7.4 Podands containing the biphenyl or binaphthyl subunit [326]
  7.5 Open-chained esters, ketones, and carbamates [326]
  7.6 Open-chained amides [329]
  7.7 Multi-armed aromatic compounds [334]
  7.8 Miscellaneous nitrogen-containing podands [337]
  7.9 Open-chained imines [339]
  7.10 Sulfur-containing podands [340]
  7.11 Open-chained ligands containing the 2,6-pyridyl subunit [341]
  7.12 Esters of pyridine-2,6-dicarboxylic acid [343]
  7.13 Polymeric podands [344]
Chapter 8. Tables
  8.1 In-out bicyclic amines [359]
  8.2 Monocyclic cryptand precursors [360]
  8.3 Cryptands [366]
  8.4 Cascade precursors [386]
  8.5 Polycyclic cryptands and spherands [387]
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