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Catenanes, Rotaxanes, and Knots - download pdf or read online

By Gottfried Schill, Alfred T. Blomquist

ISBN-10: 0126254508

ISBN-13: 9780126254501

Natural Chemistry, quantity 22: Catenanes, Rotaxanes, and Knots offers details pertinent to the synthesis of catenanes and rotaxanes. This ebook discusses the style of interplay among the molecular subunits in catenanes within the strong, liquid, and gaseous states.

Organized into 19 chapters, this quantity starts with an outline of the assumption of synthesizing molecules composed of separate entities which are automatically hooked up to each other. this article then examines the stereochemistry and the opposite actual and chemical houses regarding the mechanical connections in those compounds. different chapters give some thought to the selection of absolutely the configuration of catenanes through extension of the Cahn–Ingold–Prelog principles. This e-book discusses in addition the bond that robotically connects the catenated earrings. the ultimate bankruptcy offers with the version reports of the synthesis of knots, double wound rotaxanes, and better linear catenanes.

This booklet is a priceless source for chemists, scholars, and examine staff.

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Extra resources for Catenanes, Rotaxanes, and Knots

Example text

THE SYNTHESIS OF CATENANES R D 58 57 î î R D A R +BH 59 C 60 <*â 63 -R D R 61 62

Toluenesulfonamidodecane was cyclized with 1,10-dibromodecane in tetrahydrofuran/butanol in the presence of sodium butoxide. The cyclization was carried out with 38 % yield by means of the dilution method according to Ziegler and Orth. 89 The cleavage of the sulfonamide substrates with hydrobromic acid could only be accomplished with moderate yield. Higher yield of the macrocycle 75 could be achieved after the method of Stetter and Marx 90 in which the cyclic diamide from 1,10-diaminodecane and sebacic acid chloride is reduced with L1AIH4 in tetrahydrofuran.

After the hydrolysis of the obtained enaminonitrile with sulfuric acid and remethylation, the reaction product was analyzed with column and thin-layer chromatography. Only the main part of the reaction product, which was equivalent to 52 % yield, showed a carbonyl band in the IR spectrum. Proof that this compound was the extraannular ketone 141, was obtained by cleaving the aryl-nitrogen bond according to the method of Schill. -benzoquinone 14216 and the macrocyclic 54 134: R = C1 § 8 . 2. SCHEME 2 141 Il X < 143: R = H 1-H 142 II *N 144: R = Ac 145 55 56 8.

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Catenanes, Rotaxanes, and Knots by Gottfried Schill, Alfred T. Blomquist


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