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  • 1
    Electronic Resource
    Electronic Resource
    Tin for Organic Synthesis, 12. Synthesis of Aromatic and Olefinic Sodium Sulfonates by Electrophilic Destannylation with Trimethylsilyl Chlorosulfonate (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 575-580 
    Details
    ISSN: 0009-2940
    Keywords: Electrophilic aromatic substitution ; Electrophilic vinylic substitution ; Trialkylstannanes, application of ; Arylsulfonates, sodium salts of ; Vinylsulfonates, sodium salts of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A mild and effective method for the preparation of a variety of aromatic, olefinic, and acetylenic sodium sulfonates is described. The reaction of trialkylaryl- (2a-k) and -heteroarylstannanes (4a-d), bis-(1-alkenyl)dibutylstannanes (6a-f), or trialkylalkynylsta manes with trimethylsilyl chlorosulfonate (1) followed by hydrolysis with aqueous NaHCO3 provides the sodium sulfonates in an ipso-specific and in the case of vinylic stannanes stereospecific manner. A comparison of the reactivity of stannylated and silylated olefinic compounds 13 and 14 underlines the greater leaving ability of the stannyl moiety. The in situ preparation of the stannanes makes it possible to apply the synthetic method to natural products such as N-substituted apocodeine (17).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280609
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  • 2
    Electronic Resource
    Electronic Resource
    Tin for Organic Synthesis, 14Part 13: Ref.. Synthesis of Aromatic and α,β-Unsaturated Aldehydes by a Friedel-Crafts-like Electrophilic Destannylation Using 1,1-Dichloromethyl Methyl Ether (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 45-51 
    Details
    ISSN: 0009-2940
    Keywords: Electrophilic aromatic substitution ; Electrophilic vinylic substitution ; Aromatic aldehydes ; α,β-Unsaturated aldehydes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A mild and effective method for the preparation of a variety of aromatic (7a-m), heteroaromatic (7n-r), and α,β-unsaturated aldehydes (8a-f) is described. The reaction of trialkylaryl- (2a-o), heteroaryl- (2p-t), and 1-alkenylstannanes (4a-f and 5a-f) with dichloromethyl methyl ether (1, DCME) in the presence of aluminium trichloride followed by hydrolysis provides the corresponding aldehydes. In the case of arylstannanes the ipso-isomers are generally formed; the p-alde-hydes occur as side products. The electrophilic substitution of 1-alkenylstannanes with 1 leads to α,β-unsaturated aldehydes in an ipso- and stereospecific manner. A comparison of the leaving abilities of the stannyl and silyl groups shows a lower or even zero reactivity of the silyl-substituted compounds 6a-c towards the electrophile 1. In the silylstannylal-kene 6c only the stannyl group reacts whereas the stannyl function remains unaffected in the product, aldehyde 11.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961290111
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  • 3
    Electronic Resource
    Electronic Resource
    Tin for Organic Synthesis, 5 A New and Regioselective Synthesis of Aromatic Diazene Derivatives (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2297-2301 
    Details
    ISSN: 0009-2940
    Keywords: Aromatic substitution, electrophilic ; Azo compounds, synthesis of ; Diazonium compounds, aromatic, coupling reaction of, with trialkylarylstannanes ; Trialkylarylstannanes, application of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new method for the preparation of aromatic diazene derivatives 3a  -  1, 5, 7a, b, 9 under very mild conditions is described. The reaction of trialkylarylstannanes with nitro-substituted benzenediazonium tetrafluoroborates leads, by strict ipso substitution, to the corresponding diaryldiazenes in satisfactory to high yields. Due to the excellent leaving group quality of the stannyl group azo compounds may be prepared which are not accessible by normal electrophilic azo coupling. The products can be valuable precursors, obtained by reduction to the amines or other derivatizations, for consecutive aromatic compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911241023
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  • 4
    Electronic Resource
    Electronic Resource
    Tin for Organic Synthesis, 7. New Regioselective Syntheses of Diaryl Sulfones, Arenesulfonamides, and Arenesulfonic Acid Sodium Salts (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 763-768 
    Details
    ISSN: 0009-2940
    Keywords: Aromatic substitution, electrophilic ; Sulfones, synthesis of ; Sulfonamides, synthesis of ; Sulfonic acids, sodium salts, synthesis of ; Stannanes, trialkylaryl-, application of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of (trialkylstannyl)arenes 1 with corresponding reagents containing a chlorosulfonyl group leads, by exclusive ipso substitution, to important diaryl sulfones 2a - i, N1-alkyl-arenesulfonamides 8a - f, and sodium arenesulfonates 13a - c in high yields under mild conditions. The specific leaving ability of the stannyl group allows, moreover, the preparation of arylsulfonyl isomers which are not accessible under the influence of the conventional directing forces of substituents. With N, N1-dialkylamidosulfonyl chloride/AlCl3 complexes no destannylation takes place, but the first intramolecular sulfonyltin complex 11 is formed. This result is used to discuss details of the mechanism involved.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260329
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  • 5
    Electronic Resource
    Electronic Resource
    Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 1131-1136 
    Details
    ISSN: 0009-2940
    Keywords: Electrophilic vinylic substitution ; Isocyanates ; α,β-Unsaturated amides, synthesis of ; Carbodestannylation ; Alkenylstannanes, applications of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new and effective method for the preparation of a variety of olefinic carboxamides 6a-k and N-(4-methylphenyl-sulfonyl) carboxamides 7a-d is described. The reaction of aryl and alkyl isocyanates 4a-c or 4-methylphenylsulfonyl isocyanate 5 with 1-alkenyltrialkylstannanes 1a-e and di-1-alkenyldibutylstannanes 2a-c in the presence of aluminium trichloride provides the corresponding N-aryl-substituted olefinic carboxamides 6a-k or the N-(4-methylphenyl-sulfonyl)-substituted olefinic carboxamides 7a-d in good yields. The stannyl moiety is superior to hydrogen as a leaving group and enables electrophilic ipso substitution at the vinylic system. In the case of di-1-alkenyldibutylstannanes the substitutions are also stereospecific, whereas the reactions of 1-alkenyltrialkylstannanes with isocyanates proceed with partial isomerisation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270625
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  • 6
    Electronic Resource
    Electronic Resource
    Tin for Organic Synthesis, 13Part 12: Ref.. A New and Regioselective Method for the Synthesis of Aromatic, Heteroaromatic, and Olefinic Sulfonamides by Electrophilic Destannylation (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 1195-1198 
    Details
    ISSN: 0009-2940
    Keywords: Electrophilic aromatic substitution ; Electrophilic vinylic substitution ; Trialkylstannanes, application of ; Sulfonamides, synthesis of ; Sulfodestannylation, application of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A mild and effective method for the preparation of aromatic and olefinic sulfonamides is described. The reaction of trialkylaryl- (4a-f), heteroaryl- (4g), and vinylic stannanes (4h) with sulfuryl chloride and secondary amines provides the corresponding sulfonamides in an ipso-specific manner.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951281210
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