Synthesis of a Crown Ether with D2 Symmetry.

Frantsi, Marianne; Lindsten, Göran; Wennerström, Olof; Mörch, Lars; Norin, T.; Wijekoon, Donald; Ulff, Bengt

doi:10.3891/acta.chem.scand.36b-0135

Cited by 9 publications

(1 citation statement)

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“…The parent system of 1, 1,2-benzodithiino [5,4,3-cde][1,2]-benzodithiin (8) has been synthesized by De Lucchi et al [6] Starting from 2,2Ј,6,6Ј-tetrahydroxybiphenyl (5) [7] , 8 was prepared by this route in four steps which involved the rearrangement of the 2,2Ј,6,6Ј-tetrakis[(dimethylamino)thiocarbonyloxy]biphenyl (6) to the 2,2Ј,6,6Ј-tetrakis[(dimethylamino)carbonylthio]biphenyl (7) and subsequent hydrolysis and air oxidation of 7 to 8. The synthetic bottle neck in this route was the reaction of 5 with dimethylthiocarbamoyl chloride which gave 6 in only 18% yield.…”

Section: Synthesis Of Compoundmentioning

confidence: 99%

Syntheses and Properties of S2-Bridged Benzidines

Zhu‐Ohlbach

Gleiter²,

Röminger

et al. 1998

Eur. J. Org. Chem.

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The syntheses of 1,2‐benzodithiino[5,4,3‐cde][1,2]benzodithiin‐2,7‐diamine (1) and dithio‐bridged benzidine 2 have been achieved. The starting material for the synthesis of 1 was 1,3‐diiodo‐5‐nitrobenzene (15) which was transformed by conventional means into 1,2‐bis[3,5‐bis(ethylthio)phenyl]diazane (19). The benzidine rearrangement of 19 in the presence of HBF4 at –30 °C yielded 4,4′‐diamino‐2,2′,6,6′‐tetraethylthiobiphenyl (20) in 50 % yield. Treatment of 20 with sodium in ammonia and work‐up in the presence of air yielded 1. The latter compound could be reduced with LiAlH4 to the tetrathiol 20a. The starting material for the preparation of 2 was 3‐chloro‐1‐iodo‐5‐nitrobenzene (23), a side product of the preparation of 15. It was transformed analogously to the preparation of 1 into 1,2‐bis(3‐ethylthiophenyl)diazane (28). The benzidine rearrangement of 28 in presence of HBF4 at –30 °C afforded 4,4′‐diamino‐2,2′‐bis(ethylthio)biphenyl (29) in 49 % yield. Treatment of 29 with sodium in ammonia and work‐up under aerobic conditions yielded 2. Quantitative reduction of 2 to the thiol 29a could be achieved with LiAlH4. The reversible electrochemical reduction of 1 on unmodified glassy carbon electrodes leads to a product to which the structure of 3 was assigned.

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Section: Synthesis Of Compoundmentioning

confidence: 99%

Syntheses and Properties of S2-Bridged Benzidines

Zhu‐Ohlbach

Gleiter²,

Röminger

et al. 1998

Eur. J. Org. Chem.

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ChemInform Abstract: SYNTHESIS OF A CROWN ETHER WITH D2 SYMMETRY

Frantsi¹,

Lindsten²,

Wennerstroem³

1982

Chemischer Informationsdienst

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Lipophile Kronenverbindungen — selektive Extraktionsmittel für Metallionen; Syntheseprinzipien

Beger

Gloe²

1986

Zeitschrift fuer Chemie

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Lipophilic crown ethers are useful for metal ion extraction: they are soluble in organic phases and insoluble in aqueous ones. The lipophilicity can be enhanced by long‐chain hydrocarbon residues, by expanding the carbon content in the crown skeleton and by other structural variations. The complexation behaviour and, therefore, the selectivity of crowns in extraction processes can be altered by changing the crown diameter, the kind and the number of hetero atoms within the crown ring or at positions outside the cycle. Furthermore, for the electro‐neutrality of the extracted species it is necessary to transfer also an anion into the organic phase. This problem can be solved with crown ether acids or with other hydrophobic inorganic or organic anions. In this review with 276 references many synthetic routes and examples of such lipophilic crown ethers are described. Special attention is given to the building blocks for the crown ethers, which are important in the extraction area. So the survey should open a view for similar syntheses of new metal extraction reagents with coronand structure.

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Synthesis of a Crown Ether with D2 Symmetry.

Cited by 9 publications

References 0 publications

Syntheses and Properties of S2-Bridged Benzidines

Syntheses and Properties of S2-Bridged Benzidines

ChemInform Abstract: SYNTHESIS OF A CROWN ETHER WITH D2 SYMMETRY

Lipophile Kronenverbindungen — selektive Extraktionsmittel für Metallionen; Syntheseprinzipien

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