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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and Thiophene Ring Opening Reaction of [2]Paracyclo[2](2,5)-and -(2,4)thiophenophanes (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1403-1409 
    Details
    ISSN: 0009-2940
    Keywords: Paracyclothiophenophane ; Photodesulfurization ; Pyrolysis ; Reductive ring opening reaction ; [n] Paracyclophane ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dithia[3]paracyclo[3](2,4)- and -(2,5)thiophenophanes 〈dithia-[3.3](2,4)- and -(2.5)PTP〉 (3, 7, 9) are obtained by the coupling reaction of the corresponding bis(chloromethyl)- and bis(mercaptomethyl)arenes. Desulfurization of the dithia[3.3]PTPs 3, 7, 9 by photolysis affords the thia[2.3]PTPs 15, 16, 17 and [2.2]PTPs 14, 18, 19, 20 The pyrolysis of the disulfone 12 gives the symmetrical thiophenophane 13. The dynamics of the ring inversion, the UV spectra, and the reductive ring opening with Raney-Ni (W-7) of the obtained PTPs are discussed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240614
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  • 2
    Electronic Resource
    Electronic Resource
    4H,5H-Benzo[1,2-c;3,4-c′]bis[1,2,5]thiadiazole-4,5-dione (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 2767-2769 
    Details
    ISSN: 0009-2940
    Keywords: 4H,5H-Benzo[1,2-c;3,4-c′]bis[1,2,5]thiadiazole-4,5-dione ; 5,6-Dihydroxybenzenetetramine ; 5,6-Dimethoxybenzenetetramine ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 4H,5H-Benzo[1,2-c;3,4-c′]bis[1,2,5]thiadiazole-4,5-dione (2) was prepared by oxidation of 4-bromobenzobis[1,2,5]thiadiazole (3d) with nitric acid and subsequently converted into 5,6-dihydroxybenzenetetramine dihydrochloride (10) and the dimethoxy derivative 13. Treatment of the 4-hydroxy derivative 3a with chromium(VI) reagents led to cleavage of the benzene ring, giving dicarboxylic acid 4.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931261230
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  • 3
    Electronic Resource
    Electronic Resource
    Medium-Sized Cyclophanes, 20. Synthesis and Conformational Studies of syn- and anti-Dihydroxy[n.2]metacyclophanes (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 2443-2454 
    Details
    ISSN: 0009-2940
    Keywords: Hydroxy[n.2]metacyclophanes ; Pyrolysis ; trans-tert-Butylation ; syn- and anti-Conformers ; Ring inversion ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: syn- and anti-Dimethoxy[n.2]metacyclophanes 9 are obtained by pyrolysis of the corresponding anti-sulfones 8, which are prepared by the reaction of 1,n-bis[3-(chloromethyl)-2-methoxyphenyl]alkanes 6 with Na2S in ethanol under the high dilution conditions, followed by the oxidation of the obtained thiametacyclophanes 7 with m-chloroperbenzoic acid. Demethylation of anti-dimethoxy[n.2]metacyclophanes anti-9 with BBr3 in dichloromethane affords the corresponding anti-dihydroxy[n.2]metacyclophanes anti-10. On the other hand, demethylation of syn-dimethoxy[3.2]-syn- 9b and -[4.2]meta-cyclophane syn-9c gives syn-dihydroxy[n.2]metacyclophanes syn-10b, c, but syn-dimethoxy[5.2]-syn-9d and -[6.2]metacyclophane syn-9e are converted into the corresponding anti-dihydroxy[n.2]metacyclophanes anti-10d, e. AlCl3 · CH3NO2-catalyzed de-tert-butylation of tert-butyl-syn- and -anti-dihydroxy[3.2]- and -[4.2]metacyclophanes syn/anti-10b, c has been carried out in benzene to give the desired metacyclophanes anti-11a-c and syn-11c except syn-dihydroxy-[3.2]metacyclophane syn-11b which is converted into 8,17-epoxy[3.2]metacyclophane 13. The assignment of syn and anti conformations has been confirmed by 1H-NMR analyses and X-ray diffraction studies. The dynamics of the ring inversion and UV spectra are also discussed.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921251116
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    Paper (German National Licenses)
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