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Volumn 3, Issue 11, 2001, Pages 1777-1780

Stereospecific Anionically Promoted Transannular Hydride Shifts in Medium-Ring Hydroxy Ketones. Probe of Their Reversibility and the Potential for Regiocontrol

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE;

EID: 0035979095     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0100733     Document Type: Article
Times cited : (8)

References (36)
  • 13
    • 0011863061 scopus 로고
    • The reaction of 3 with a primary amine constitutes an interesting variant: (a) Wiseman, J. R.; Lee, S. Y. J. Org. Chem. 1986, 51, 2485.
    • (1986) J. Org. Chem. , vol.51 , pp. 2485
    • Wiseman, J.R.1    Lee, S.Y.2
  • 16
    • 0041703934 scopus 로고
    • Hemiketal 3 shows no carbonyl band in the infrared [Quinn, C. B.; Wiseman, J. R. J. Am. Chem. Soc. 1973, 95, 1342]. Nevertheless, both tautomers can be brought into reaction depending upon the specific transformation in question: (a) Braish, T. F.; Fuchs, P. L. Synth. Commun. 1986, 16, 111.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 1342
    • Quinn, C.B.1    Wiseman, J.R.2
  • 17
    • 0000144387 scopus 로고
    • Hemiketal 3 shows no carbonyl band in the infrared [Quinn, C. B.; Wiseman, J. R. J. Am. Chem. Soc. 1973, 95, 1342]. Nevertheless, both tautomers can be brought into reaction depending upon the specific transformation in question: (a) Braish, T. F.; Fuchs, P. L. Synth. Commun. 1986, 16, 111.
    • (1986) Synth. Commun. , vol.16 , pp. 111
    • Braish, T.F.1    Fuchs, P.L.2
  • 21
    • 84977283160 scopus 로고
    • 6-Hydroxycyclodecanone exists in the hemiacetal form to the extent of 39-77% depending upon solvent [Mijs, W. J.; De Vries, K. S.; Westra, J. G.; Gaur, H. A. A.; Smidt, J.; Vriend, J. Recl. Trav. Chim. Pays-Bas 1968, 87, 580]. For representative reactions of this substance, consult: (a) Thies, R. W.; Yue, S. T. J. Org. Chem. 1982, 47, 2681.
    • (1968) Recl. Trav. Chim. Pays-Bas , vol.87 , pp. 580
    • Mijs, W.J.1    De Vries, K.S.2    Westra, J.G.3    Gaur, H.A.A.4    Smidt, J.5    Vriend, J.6
  • 22
    • 0042204370 scopus 로고
    • 6-Hydroxycyclodecanone exists in the hemiacetal form to the extent of 39-77% depending upon solvent [Mijs, W. J.; De Vries, K. S.; Westra, J. G.; Gaur, H. A. A.; Smidt, J.; Vriend, J. Recl. Trav. Chim. Pays-Bas 1968, 87, 580]. For representative reactions of this substance, consult: (a) Thies, R. W.; Yue, S. T. J. Org. Chem. 1982, 47, 2681.
    • (1982) J. Org. Chem. , vol.47 , pp. 2681
    • Thies, R.W.1    Yue, S.T.2
  • 27
    • 0042705586 scopus 로고    scopus 로고
    • note
    • In the intramolecular variants, neither of the two functional groups is present in excess and no volatile byproduct is generated as reaction progresses.
  • 35
    • 0043206693 scopus 로고    scopus 로고
    • note
    • At ordinary temperatures, 9 is constituted of a mixture of two atropisomers in which the carbonyl group is projected in either an upward or downward direction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.