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  • 4-Thiazolidinones  (1)
  • Dimethylaminobis(trifluoromethyl)borane  (1)
  • 1995-1999  (2)
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  • 1995-1999  (2)
Year
  • 1
    ISSN: 0009-2940
    Keywords: Dimethylaminobis(trifluoromethyl)borane ; Nitriles ; Cyclopropanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dimethylaminobis(trifluoromethyl)borane, (CF3)2BNMe2 (A), reacts with Cl(CH2)3CN to yield [Cl(CH2)2CH(CN)](CF3)2B·NHMe2 (1) whereas Br(CH2)3CN and A combine in a 1:2 ratio to form [cyclo-C3H4(CN)](CF3)2B·NHMe2 (2) and Br(CF3)2B·NHMe2. Br(CH2)nCN and A yield [Br(CH2)n-1 CH-(CN)](CF3)2B·NHMe2, n=4 (3), n=5 (4) and n=6 (5). Compound 2 and (NCCH2)CF3)2B·NHMe2 can be alkylated at nitrogen with CH3I/KOH in ether to yield [cyclo-C3H4(CN)]-(CF3)2B·NMe3 (6) and (NCCH2)(CF3)2B·NMe3 (7), respectively. treatment of 1 and 3 with hydroxide in ether gives the respective five- and six-membered heterocycles (CF3)2 (8) and (9). Reduction of the nitrile group with (iBu)2Alh in CH2Cl2 at -50°C followed by hydrolysis furnishes the corresponding aldehydes (OCHCH2) (CF3)2B·NMe3 (10), [cyclo-C3H4(CHO)](CF3)2B·NMe3 (11) and (12). The structure of 2 was determined by an X-ray investigation.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1427-1431 
    ISSN: 0947-3440
    Keywords: 4-Thiazolidinones ; L-Menthone spiro acetals ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: By acetalisation of L-menthone (2) with mercaptoacetic acid and derivatives of benzylamine, the spirocyclic N,S-acetals 3 were obtained as single diastereomers. The reaction of an epimeric mixture of unsubstituted thiazolidinones 4 with acetic anhydride or allyl iodide afforded homochiral N-acetyl (5) or N-allyl N,S-acetals (6), respectively. The configuration of the new stereogenic centres were proven by X-ray crystallography.
    Type of Medium: Electronic Resource
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