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Volumn 53, Issue 22, 1997, Pages 7557-7576

Tandem Wolff rearrangement-'tert-amino effect' sequence: Synthesis of 2-oxoindolinium enolate derivatives

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PIPERIDINE DERIVATIVE;

EID: 0342546632     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00448-1     Document Type: Article
Times cited : (20)

References (47)
  • 4
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    • 2 proton to a highly basic central allenic carbon atom has been observed in the thermal isomerization of 1-morpholino-3-phenyl(or vinyl) allenes. See: Mayer, T.; Maas, G. Tetrahedron Lett. 1992, 33, 205-208.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 205-208
    • Mayer, T.1    Maas, G.2
  • 15
    • 0003828015 scopus 로고
    • Wiley: New York
    • Tidwell, T.T. Ketenes, Wiley: New York, 1995, p. 78.
    • (1995) Ketenes , pp. 78
    • Tidwell, T.T.1
  • 16
    • 0000936734 scopus 로고
    • For reviews concerning ammonium ylides, see: a) Padwa, A., Hornbuckle, S.F. Chem. Rev. 1991, 91, 263-309.
    • (1991) Chem. Rev. , vol.91 , pp. 263-309
    • Padwa, A.1    Hornbuckle, S.F.2
  • 32
    • 0342727967 scopus 로고    scopus 로고
    • note
    • The X ray data of 4a and 5a are registered at the Cambridge Cristallographic Data Centre, Cambridge (U.K.).
  • 33
    • 0343597956 scopus 로고    scopus 로고
    • note
    • The N(1)C(2)C(3)C(3a)C(7a) ring is almost planar, the C(7a) atom being at a distance of 0.027 Å from the N(1)C(2)C(3)C(3a) mean plane. The dihedral angle between the C(3a)C(4)C(5)C(6)C(7)C(7a) and N(1)C(2)C(3)C(3a)C(7a) planes is 1.10°. The piperidinium ring adopts a perfect chair conformation; the dihedral angle between his mean plane and the N(1)C(2)C(3)C(3a)C(7a) mean plane is 88.84°.
  • 34
    • 0343162576 scopus 로고
    • Bond lenghts in crystalline organic compounds
    • 72nd Edition CRC Press
    • Handbook of Chemistry and Physics; Lide, D.R., Editor-in-Chief; 72nd Edition 1991-1992, CRC Press. Bond lenghts in crystalline organic compounds 9-3 to 9-17.
    • (1991) Handbook of Chemistry and Physics , pp. 93-917
    • Lide, D.R.1
  • 38
    • 0343162566 scopus 로고
    • b) Zvilichovsky, G.; Gurvich, V.; Cohen, S. J. Chem. Research (S) 1994, 335; J. Chem. Research (M) 1994, 1801-1812.
    • (1994) J. Chem. Research (M) , pp. 1801-1812
  • 42
    • 84970624336 scopus 로고
    • a) Heard, G.L.; Yates, B.F. Aust. J. Chem. 1994, 47, 1685-1694 and 1995, 48, 1413-1423.
    • (1995) Aust. J. Chem. , vol.48 , pp. 1413-1423
  • 44
    • 0342292919 scopus 로고    scopus 로고
    • note
    • When a toluenic solution of the ylide 5a was refluxed for 24 h, no transformation into the mesoionic compound 4a was observed.
  • 45
    • 0342727932 scopus 로고    scopus 로고
    • note
    • For instance as described in ref. 6a, refluxing the mesoionic compound XI (see structure in Table 2) in toluene yielded a bridgehead lactam through a [1,3] shift.
  • 47
    • 0000356528 scopus 로고    scopus 로고
    • For explosive hazard of diazotransfer reagents, see: Bollinger, F.W.; Tuma, L.D. Synlett, 1996, 407-413.
    • (1996) Synlett , pp. 407-413
    • Bollinger, F.W.1    Tuma, L.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.