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Volumn 54, Issue 40, 1998, Pages 12151-12160

The chemistry of 2-alkenyl-5(4H)-oxazolones. VIII acid-catalyzed reaction with alcohols

Author keywords

[No Author keywords available]

Indexed keywords

2 ALKENYL 5(4H) OXAZOLONE DERIVATIVE; ALCOHOL DERIVATIVE; OXAZOLONE; UNCLASSIFIED DRUG;

EID: 0032192379     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00751-0     Document Type: Article
Times cited : (18)

References (32)
  • 11
    • 4243971673 scopus 로고
    • 7. Heilmann, S.M.; Moren, D.M.; Rasmussen, J.K.; Krepski, L.R.; Pathre, S.V. U.S. Patent 5,081,197 1992; Chemical Abstracts 1992, 116, P129912s.
    • (1992) Chemical Abstracts , vol.116
  • 16
    • 4243902646 scopus 로고
    • 10. McEntire, E.E.; Sellstrom, K.B.; Nieh, E.C.Y.; Livington, D.R. U.S. Patent 4, 492,801 1985; Chemical Abstracts 1985, 102, P45495f.
    • (1985) Chemical Abstracts , vol.102
  • 17
    • 85038546828 scopus 로고    scopus 로고
    • Fractional atomic charges were computed using the the Gaussian 94 for Windows (revision E. 1) Program and an Intel Pentium 200 MHz Personal Computer. The computations were unconstrained and the geometries were true minima
    • 11. Fractional atomic charges were computed using the the Gaussian 94 for Windows (revision E. 1) Program and an Intel Pentium 200 MHz Personal Computer. The computations were unconstrained and the geometries were true minima.
  • 18
    • 0000856602 scopus 로고
    • A of its conjugate acid. Reference 4, however, provided data in support of a value < 5. Furthermore, the value of 5.59 reported for an analogous oxazoline would support a value in the range of 3-5 pK units. Clearly, acids such as ethanesulfonic acid and TFA should be sufficiently strong to protonate the oxazolone
    • A of its conjugate acid. Reference 4, however, provided data in support of a value < 5. Furthermore, the value of 5.59 reported for an analogous oxazoline (Weinberger, M.A.; Green halgh, R. Can. J. Chem. 1963, 41, 1038-1041) would support a value in the range of 3-5 pK units. Clearly, acids such as ethanesulfonic acid and TFA should be sufficiently strong to protonate the oxazolone.
    • (1963) Can. J. Chem. , vol.41 , pp. 1038-1041
    • Weinberger, M.A.1    Green Halgh, R.2
  • 19
    • 85038541376 scopus 로고    scopus 로고
    • There were no remarkable differences in the IR spectra of 1a and 1b suggestive of a lack of coplanarity of the alkenyl and C=N units
    • 13. There were no remarkable differences in the IR spectra of 1a and 1b suggestive of a lack of coplanarity of the alkenyl and C=N units.
  • 21
    • 85038540039 scopus 로고    scopus 로고
    • 1a was not examined in this study because of competitive Michael addition
    • 15. 1a was not examined in this study because of competitive Michael addition.
  • 22
    • 85038548227 scopus 로고    scopus 로고
    • The 1:1:1 stoichiometry was utilized so that reasonable quantities of the ring opened product derived from the less reactive oxazolone would be formed and facilitate quantification
    • 16. The 1:1:1 stoichiometry was utilized so that reasonable quantities of the ring opened product derived from the less reactive oxazolone would be formed and facilitate quantification.
  • 26
    • 0002664833 scopus 로고
    • A critical compilation of substituent constants
    • Chapman, N.B.; Shorter, J., Eds.: Plenum Press: London, Chapter 10
    • 19. Exner, O. A Critical Compilation of Substituent Constants. In Correlation Analysis in Chemistry; Chapman, N.B.; Shorter, J., Eds.: Plenum Press: London, 1978, Chapter 10, pp. 439-540.
    • (1978) Correlation Analysis in Chemistry , pp. 439-540
    • Exner, O.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.