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Volumn , Issue 9, 2006, Pages 1423-1426

New highly efficient method for the synthesis of tert-alkyl nitroso compounds

Author keywords

Benzoyl peroxide; Selective oxidation; Steric hindrance; Tert alkyl amines; Tert alkyl nitroso compounds

Indexed keywords

ALKYLATION; AMINES; BENZENE; HYDROPHOBICITY; OXIDATION; PEROXIDES; PURIFICATION; SYNTHESIS (CHEMICAL);

EID: 33646581396     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926442     Document Type: Article
Times cited : (8)

References (45)
  • 12
    • 33646568998 scopus 로고    scopus 로고
    • note
    • USD 285.80 for 5 g (ALDRICH 2005-2006).
  • 22
    • 0004485595 scopus 로고
    • 3CN=O is described but no detailed procedure is given: Chiarelli, R.; Rassat, A. Tetrahedron 1973, 29, 3639.
    • (1973) Tetrahedron , vol.29 , pp. 3639
    • Chiarelli, R.1    Rassat, A.2
  • 24
    • 0003199590 scopus 로고
    • Wiley: New York
    • A laborious 3-step preparation of the product A on a large scale via the hydroxylamine 3a is described: Calder, A.; Forrester, A. R.; Hepburn, S. P. Org. Synth. Coll. Vol. VI; Wiley: New York, 1972, 803.
    • (1972) Org. Synth. Coll. , vol.6 , pp. 803
    • Calder, A.1    Forrester, A.R.2    Hepburn, S.P.3
  • 30
    • 33646560825 scopus 로고    scopus 로고
    • note
    • -).
  • 34
    • 33646591131 scopus 로고    scopus 로고
    • note
    • 2K with the starting tert-butylamine (1a) remaining intact.
  • 35
    • 33646543620 scopus 로고    scopus 로고
    • note
    • 3 was efficient enough to provide a complete conversion of the more hydrophobic amine 1c to the benzoyl derivative 2c. Apparently, a fine balance between hydrophilicity, basicity and aqueous solubility precluded the formation of the respective tert-alkyl-ammonium benzoate under the reaction conditions.
  • 37
    • 33646567992 scopus 로고    scopus 로고
    • note
    • Dimerization time and hence the crystallization time dramatically increases with the increase of the steric demands of the tert-alkyl substituent: ca. 20-30 min for A, several hours in the refrigerator (+4 °C) for B, and at least a week in a deep freezer (-18 °C) for C. For the NMR study on the monomer-dimer equilibrium, see ref. 10a.
  • 38
    • 33646557212 scopus 로고    scopus 로고
    • note
    • NMR monitoring of the blue liquid nitroso monomer C prior to the crystallization showed that it was sufficiently pure to be used as a reactant in subsequent transformations.
  • 44
    • 33646564587 scopus 로고    scopus 로고
    • note
    • The research on new type of metal-free nitrogen bases is currently in progress in our laboratory.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.