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Volumn 62, Issue 8, 2006, Pages 1772-1776

Bromination of α-tocopherol methano-dimer and ethano-dimer

Author keywords

Bromination; Reaction mechanism; Tocopherol; Tocopherol dimers; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL DERIVATIVE; DIMER;

EID: 31544455007     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.050     Document Type: Article
Times cited : (10)

References (28)
  • 9
    • 31544478778 scopus 로고    scopus 로고
    • note
    • The preparation is given in Ref. 5b.
  • 10
    • 31544451502 scopus 로고    scopus 로고
    • Unpublished results.
    • T. N., Unpublished results.
  • 11
    • 31544481133 scopus 로고    scopus 로고
    • note
    • The small amount of HBr generated from TMS-Br and water in solvents (not specially dried) is sufficient. All syntheses used RRR-tocopherols as starting materials. It was not tested whether the integrity of stereochemistry was maintained over the reaction steps.
  • 12
    • 13844254623 scopus 로고    scopus 로고
    • The issue of the two diastereomers formed by attack of the phenolic OH at either side of oQM-1 and their interconversion has been discussed, and also a full NMR assignment is given: H. Schröder, and T. Netscher Magn. Reson. Chem. 39 2001 701 708
    • (2001) Magn. Reson. Chem. , vol.39 , pp. 701-708
    • Schröder, H.1    Netscher, T.2
  • 14
    • 0030837379 scopus 로고    scopus 로고
    • A similar reaction between para-tocopherylquinone and TMS halides has been used to obtain the O-TMS-protected 5a-bromo-α-tocopherol: T. Rosenau, and W.D. Habicher Tetrahedron Lett. 38 1997 5959 5960
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5959-5960
    • Rosenau, T.1    Habicher, W.D.2
  • 15
    • 31544438530 scopus 로고    scopus 로고
    • Authentic material was available from earlier work: see the first publication in Ref. 9.
    • Authentic material was available from earlier work: see the first publication in Ref. 9.
  • 16
    • 31544441598 scopus 로고    scopus 로고
    • note
    • #)/R, and thus the difference of activation energies.
  • 17
    • 31544470868 scopus 로고    scopus 로고
    • note
    • It should be noted that this mechanism is still a proposal only. Clarifying computations are underway.
  • 21
    • 31544441889 scopus 로고    scopus 로고
    • note
    • The use of ICl or IBr had no effect on the outcome of the low-temperature route leading to 11.
  • 22
    • 31544482635 scopus 로고    scopus 로고
    • note
    • Possible erosion of the stereochemistry, especially at C-2, as a consequence of the chemical manipulations was not further studied. However, comparison of the spiro-dimeric products with stereochemically pure (all-R)-compounds gave no indication of such a process.
  • 25
    • 4243553426 scopus 로고
    • A. Becke Phys. Rev. A38 1988 3098 3100
    • (1988) Phys. Rev. , vol.38 , pp. 3098-3100
    • Becke, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.