메뉴 건너뛰기




Volumn 70, Issue 12, 2005, Pages 4720-4725

A one-pot isomerization-arylation of 2,3-epoxycyclohexanone under controlled microwave heating

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; KETONES; MICROWAVE HEATING; POLYETHYLENE GLYCOLS; REACTION KINETICS; SODIUM COMPOUNDS;

EID: 20344370975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0504619     Document Type: Article
Times cited : (21)

References (42)
  • 4
    • 20344404872 scopus 로고    scopus 로고
    • note
    • a value of 1,2-cyclohexanedione has been determined to 9.9 by a potentiometric method, see ref 3.
  • 5
    • 84944048121 scopus 로고
    • Katritzky, A. R., Ed.; Pergamon Press: New York
    • Porter, A. E. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon Press: New York, 1984; Vol. 3, pp 157-197.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 157-197
    • Porter, A.E.1
  • 35
    • 0037393778 scopus 로고    scopus 로고
    • 3N, and triethanolamine. For α-arylation with strong bases, see: Culkin D, A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 234-245
    • Culkin, D.A.1    Hartwig, J.F.2
  • 37
    • 20344383411 scopus 로고    scopus 로고
    • note
    • The following compounds have been tested: 2,3-epoxy-4,4- dimethylcyclohexenone, 2,3-epoxycyclopentanone, chalconoxide, and benzalacetoneoxide.
  • 38
    • 20344387367 scopus 로고    scopus 로고
    • note
    • 13C NMR peaks could be released with ether from the flash silica column after elution of 3 (corresponding to 10-40% of utilized 1).
  • 39
    • 20344378125 scopus 로고    scopus 로고
    • note
    • To determine the structure of the byproduct, the Heck reaction was performed, using an excess of 2a with 3 h of microwave heating at 180°C. Not more than 12% of the 3,6-diarylated product could be isolated.
  • 41
    • 0001045392 scopus 로고
    • Base-mediated isomerization of α,β-epoxyketones has been described but is suggested to be of minor importance in this case, see: House, H. O.; Ro, R. S. J. Am. Chem. Soc. 1958, 80, 2428-2433.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 2428-2433
    • House, H.O.1    Ro, R.S.2
  • 42
    • 20344404109 scopus 로고    scopus 로고
    • note
    • Treatment of 3a under microwave Heck conditions with sodium pivaloate in place of NaOAc did not yield 7b, ruling out the possibility that 7b may be formed through transesterification.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.