메뉴 건너뛰기




Volumn 70, Issue 24, 2005, Pages 10210-10212

IBX-mediated α-hydroxylation of α-alkynyl carbonyl systems. A convenient method for the synthesis of tertiary alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; DEHYDROGENATION; SYNTHESIS (CHEMICAL);

EID: 28044457200     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051898j     Document Type: Article
Times cited : (44)

References (40)
  • 1
    • 56249137056 scopus 로고
    • For the synthesis of IBX, see: (a) Hartmann, C.; Meyer, V. Chem. Ber. 1893, 26, 1727-1732.
    • (1893) Chem. Ber. , vol.26 , pp. 1727-1732
    • Hartmann, C.1    Meyer, V.2
  • 5
  • 9
    • 20544472300 scopus 로고    scopus 로고
    • (c) Kumar, I. Synlett 2005, 1488-1489.
    • (2005) Synlett , pp. 1488-1489
    • Kumar, I.1
  • 20
    • 28044467170 scopus 로고    scopus 로고
    • note
    • Besides the more likely SET-based mechanism, an ionic mechanism was discussed for the IBX-mediated dehydrogenation of carbonyl compounds: ref 5b.
  • 21
    • 28044457231 scopus 로고    scopus 로고
    • note
    • The reaction of p-cresol with IBX gave 4-methyl-1,2-bisphenol: ref 5b.
  • 22
    • 28044442979 scopus 로고    scopus 로고
    • note
    • The benzylic oxidation using IBX can be explained via intramolecular oxygen transfer: ref 5b.
  • 25
    • 0000271393 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: New York
    • (a) Jones, A. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 7, pp 151-191.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 151-191
    • Jones, A.B.1
  • 26
    • 0009506491 scopus 로고
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York
    • (b) Davis, F. A.; Chen, B.-C. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York, 1995; Vol. E21b, pp 4497-4518.
    • (1995) Methods of Organic Chemistry (Houben-Weyl), 4th Ed. , vol.E21B , pp. 4497-4518
    • Davis, F.A.1    Chen, B.-C.2
  • 28
    • 0001743040 scopus 로고
    • For selected examples for the synthesis of tertiary alcohols via α-hydroxylation of carbonyl compounds, see: (a) Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715-3717.
    • (1990) J. Org. Chem. , vol.55 , pp. 3715-3717
    • Davis, F.A.1    Weismiller, M.C.2
  • 31
    • 28044472813 scopus 로고    scopus 로고
    • note
    • Other hypervalent iodine compounds were not used in such α-hydroxylations.
  • 32
    • 28044446597 scopus 로고    scopus 로고
    • note
    • Ketone 1 was detected as the intermediary occurring species in the transformation 4 → 2 by capillary gas chromatography and by thin-layer chromatography.
  • 35
    • 28044455273 scopus 로고    scopus 로고
    • note
    • Adding IBX at once to the reaction mixture gave varying yields for the conversion 1a → 2b (51-88%).
  • 36
    • 28044450430 scopus 로고    scopus 로고
    • note
    • The origin of this effect remains unclear.
  • 37
    • 28044436546 scopus 로고    scopus 로고
    • note
    • A facile dehydration of the tertiary alcohols 2 giving α,β-unsaturated carbonyl compounds 3 was not observed under these conditions.
  • 38
    • 28044444133 scopus 로고    scopus 로고
    • note
    • Tertiary alcohols were not detected as intermediary species in the IBX-mediated dehydrogenation of carbonyl compounds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.