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TitleSupramolecular Chemistry I — Directed Synthesis and Molecular Recognition
Author
TagsChemistry
LanguageEnglish
File Size13.6 MB
Total Pages328
Table of Contents
                            Cover Page
Title Page
ISBN 354056280X, 038756280X
Editors
Preface
Attention all "Topics in Current Chemistry" readers
Table of Contents
Substrate-Directed Synthesis: The Rapid Assembly of Novel Macropolycyclic Structures via Stereoregular Dieis-Alder Oligomerizations
Rigid Molecular Tweezers as Hosts for the Complexation of Neutral Guests
Cyclotriveratrylenes and Cryptophanes: Their Synthesis and Applications to Host-Guest Chemistry and to the Design of New Materials
From Classical Chirality to Topologically Chiral Catenands and Knots
Recognitory Coloration of Cations with Chromoacerands
Genealogically Directed Synthesis: Starburst/Cascade Dendrimers and Hyperbranched Structures
Author Index Volumes 151-165
                        
Document Text Contents
Page 2

165 Topics in Current Chemistry

Page 164

From Classical Chirality to Topologically Chiral Catenands and Knots

L...o~/o~o-.3
8 5 ~*

K C N

o o

\ _o'- '- . o i o - - , . , /
o/ 7 o,/

/\o_J\oJ'\
o o

8 6

\ o/-°\ o~°\ / o
lo oio o/\
o o (o o~

(o o3

u 8 6 8 7

Fig. 33. a) Demetallation of the dicopper(I) trefoil knot 852 ÷ leading to the trefoil knot 86.
b) Two topological stereoisomers; trefoil knot 86 and unraveled macrocycle 87

Cu(I) complexes by KCN led to the corresponding free ligands represented in
Fig. 33. Demetallation of 85 z÷ afforded the free trefoil knot 86 as a colourless
glass. Very small amounts (0.5%) of 87, the unraveled topological diastereomer of
86 could also be isolated and characterized.

A comparison between the two isomers 86 and 87 produced strong evidence
for the knotted topology of 86. Both compounds have identical mass spectra
(FAB): molecular peaks appear at the same value. In addition, the general pattern

155

Page 165

Jean-Claude Chambron et al.

~H NMR

~ m
0 o

,oi°-~o,/°-~o/
0 0

86

8 6 + K +

m "
CHDCl z

_lL_
8 6 + K + +

(s) - (+) •

.n,i .

S ppm
' I I I I L I

8 7 6 5 4 3

156

Page 327

Author Index Volumes 151-165

Meyer, B.: Conformational Aspects of Oligosaccharides. 154, 141-208 (1990).
Misumi, S. : Recognitory Coloration of Cations with Chromoacerands. 165, 163-192 (1993).
Moffat, J. K., Helliwell, J. : The Laue Method and its Use in Time-Resolved Crystallography.

151, 61-74 (1989).
Molchanov, A. P., see Kostikov, R. R.: 155, 41-80 (1990).
Moore, T. A., see Gust, D.: 159, 103-152 (1991).

Nakamura, E., see Kuwajima, I.: 155, 1-39 (1990).

Okuda, J.: Transition Metal Complexes of Sterically Demanding Cyclopentadienyl Ligands.
160, 97-146 (1991).

Ostrowicky, A., Koepp, E., Vrgtle, F.: The "Vesium Effect": Syntheses of Medio- and
Macrocyclic Compounds 161, 37-68 (1991).

Parmon, V. N., see Lymar, S. V.: 159, 1-66 (1991).
Polian, A., see Fontaine, A.: 151, 179-203 (1989).

Raimondi, M., see Copper, D. L.: 153, 41-56 (1990).
Riekel, C. : Experimental Possibilities in Small Angle Scattering at the European Synchrotron

Radiation Facility. 151, 205-229 (1989).
Roth, H. D. : A Brief History of Photoinduced Electron Transfer and Related Reactions. 156,

1-20 (1990).
Roth, H. D.: Structure and Reactivity of Organic Radical Cations. 163, 131-245 (1992).
Riisch, M., see Warwel, S.: 164, 79-98 (!993).

Sachs, H., see John, P.: 153, 145-180 (1990).
Saeva, F. D.: Photoinduced Electron Transfer (PET) Bond Cleavage Reactions. 156, 59-92

(1990).
Sauvage, J.-P., see Chambron, J.-C.: 165, 131-162 (11993).
Sendhoff, N., see Knops, P.: 161, 1-36 (1991).
Sessler, J. L., Burrell, A. K.: Expanded Porphyrins 161, 177-274 (1991).
Sheldon, R.: Homogeneous and Heterogeneous Catalytic Oxidations with Peroxide Rea-

gents. 164, 21-43 (1993).
Sheng, R.: Rapid Ways to Recognize Kekul+an Benzenoid Systems. 153, 211-226 (1990).
Schfifer, H.-J. : Recent Contributions of Kolbe Electrolysis to Organic Synthesis. 152, 91 - 151

(1989).
Sojka, M., see Warwel, S.: 164, 79-98 (1993).
Sorba, J., see Fossey, J.: 164, 99-113 (1993).
Stanek, Jr., J.: Preparation of Selectively Alkylated Saccharides as Synthetic Intermediates.

154, 209-256 (1990).
Stoddart, J. F., see Kohnke, F. H.: 165, 1-69 (1993).
Stumpe, R., see Kim. J. I.: 157, 129-180 (1990).
Suami, T.: Chemistry of Pseudo-sugars. 154, 257-283 (1990).
Suppan, P. : The Marcus Inverted Region. 163, 95-130 (1992).
Suzuki, N.: Radiometric Determination of Trace Elements. 157, 35-56 (1990).

Thiem, J., and Klaffke, W.: Syntheses of Deoxy Oligosaccharides. 154, 285-332 (1990).
Timpe, H.-J.: Photoinduced Electron Transfer Polymerization. 156, 167-198 (1990).
Tolentino, H., see Fontaine, A.: 151, 179-203 (1989).
Tomalia, D.A.: Genealogically Directed Synthesis: Starburst/Cascade Dendrimers and

Hyperbranched Structures. 165, 193-313 (1993).
Tourillon, G., see Fontaine, A.: 151, 179-203 (1989).

Vrgtle, F., see Dohm, J.: 161, 69-106 (1991).
V6gtle, F., see Knops, P.: 161, 1-36 (1991).

318

Page 328

Author Index Volumes 151-165

V6gtle, F., see Ostrowicky, A.: 161, 37-68 (1991).
Vogler, A., Kunkeley, H. : Photochemistry of Transition Metal Complexes Induced by Outer-

Sphere Charge Transfer Excitation. 158, 1-30 (1990).
Vondenhof, M., see Mattay, J.: 159, 219-255 (1991).

Wan, P., see Krogh, E.: 156, 93-116 (1990).
Warwel, S., Sojka, M. and Riisch, M. : Synthesis of Dicarboxylic Acids by Transition-Metal

Catalyzed Oxidative Cleavage of Terminal-Unsaturated Fatty Acids. 164, 79-98 (1993).
Willner, I., and Willner, B.: Artifical Photosynthetic Model Systems Using Light-Induced

Electron Transfer Reactions in Catalytic and Biocatalytic Assemblies. 159, 153-218
(1991).

Yoshihara, K.: Chemical Nuclear Probes Using Photon Intensity Ratios. 157, 1 - 34 (1990).

Zamarev, K. I., see Lymar, S. V.: 159, 1-66 (1991).
Zamaraev, K. I., Khairutdinov, R. F.: Photoinduced Electron Tunneling Reactions in

Chemistry and Biology. 163, 1-94 (1992).
Zander, M: Molecular Topology and Chemical Reactivity of Polynuclear Benzenoid

Hydrocarbons. 153, 101-122 (1990).
Zhang, F. J., Guo, X. F., and Chen, R. S.: The Existence of Kekul~ Structures in a Benzenoid

System. 153, 181-194 (1990).
Zimmermann, S. C.: Rigid Molecular Tweezers as Hosts for the Complexation of Neutral

Guests. 165, 71-102 (1993).
Zybill, Ch.: The Coordination Chemistry of Low Valent Silicon. 160, 1-46 (1991).

319

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