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  • 1
    Electronic Resource
    Electronic Resource
    o-(α-Benzotriazolylalkyl)phenols: Versatile Intermediates for the Synthesis of Substituted Phenols (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1809-1817 
    Details
    ISSN: 0009-2940
    Keywords: Lithiation ; Mannich reaction ; Alkylation ; Grignard reaction ; Condensation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Phenols and naphthols are benzotriazolylmethylated by 1-(hydroxymethyl)-1H-benzotriazole (13) (a formaldehyde derivative) in the o- or (if both o-positions are occupied) in the p-position. The reaction can be extended to other aldehydes in the case of the naphthols. The methylene group in the o-(benzotriazolylmethyl)phenols can be lithiated (but only after trimethylsilyl protection of the hydroxy group) and then substituted by various electrophiles. The benzotriazole residues in both the primary products and in their substituted derivatives can be displaced by the alkyl anions of Grignard reagents or by hydride ions allowing the elaboration of many new types of substituted phenols.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240818
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    N-[α-(o- and p-Methoxyaryl)alkyl]benzotriazoles: Preparation and Use in Synthesis (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1819-1826 
    Details
    ISSN: 0009-2940
    Keywords: Lithiation ; Grignard reaction ; Condensation ; Aryl ethers ; Diarylmethanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Methoxybenzenes and -naphthalenes are benzotriazolylmethylated in the para-position or if this is blocked in an ortho- position. The methylene groups in the products are readily substituted by electrophiles via the lithiated derivatives. Displacement of the benzotriazole group can be effected by organometallic reagents or by electron-rich benzoid compounds to afford a versatile method for the synthesis of substituted aryl ethers.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240819
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    Paper (German National Licenses)
    Fulltext
  • 3
    Electronic Resource
    Electronic Resource
    Theoretical study of aminoalkylation in the Mannich reaction of furan with methyleneimminium salt (1998)
    New York, NY : Wiley-Blackwell
    International Journal of Quantum Chemistry 67 (1998), S. 359-366 
    Details
    ISSN: 0020-7608
    Keywords: semiempirical calculations ; solvent effects ; Mannich reaction ; reaction mechanism ; Chemistry ; Theoretical, Physical and Computational Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The potential energy surface for the reaction of furan and methyleneimminium cation with formation of a Mannich base has been studied using AM1 and PM3 semiempirical calculations. Nonspecific solvent effects were taken account of in the framework of the multicavity self-consistent reaction field approach. Characteristics of the reaction path elucidated for various media are discussed.   © 1998 John Wiley & Sons, Inc. Int J Quant Chem 67: 359-366, 1998
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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