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Volumn 59, Issue 41, 2003, Pages 8275-8284

Metalation in hydrocarbon solvents: The mechanistic aspects of substrate-promoted ortho-metalations

Author keywords

Deoligomerization; Di and tri methoxybenzenes; Hydrocarbon solvents; Metalation

Indexed keywords

1,2,4 TRIMETHOXYBENZENE; 1,3 DIMETHOXYBENZENE; BENZENE DERIVATIVE; HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; VERATROLE;

EID: 0141794090     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.07.010     Document Type: Article
Times cited : (19)

References (56)
  • 4
    • 0030593197 scopus 로고    scopus 로고
    • It is our contention that measured equivalents of THF in hydrocarbon solvents constitute catalytic systems for metalation. The metalations are greatly accelerated by the presence of small quantities of THF. Moreover, bulk (neat) THF leads to lesser extents of regiospecific metalation and the advent of secondary metalations, cf. (a) Slocum D.W., Reed D., Jackson F. III, Friesen C. J. Organomet. Chem. 512:1996;265-267
    • (1996) J. Organomet. Chem. , vol.512 , pp. 265-267
    • Slocum, D.W.1    Reed, D.2    Jackson F. III3    Friesen, C.4
  • 7
    • 85031060180 scopus 로고    scopus 로고
    • note
    • These constitute our efforts to effect atom economical metalations. cf
  • 11
    • 85031060451 scopus 로고    scopus 로고
    • No studies of 1,4-DMB are cited in Ref. 6. 1,4-DMB lies outside the scope of this investigation
    • No studies of 1,4-DMB are cited in Ref. 6. 1,4-DMB lies outside the scope of this investigation.
  • 32
    • 0037136165 scopus 로고    scopus 로고
    • This reference constitutes contribution # 1 from the Laboratory of Covalent Chemistry at Western Kentucky University
    • Slocum D.W., Ray J., Shelton P. Tetrahedron Lett. 43:2002;6071-6073. This reference constitutes contribution # 1 from the Laboratory of Covalent Chemistry at Western Kentucky University.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6071-6073
    • Slocum, D.W.1    Ray, J.2    Shelton, P.3
  • 46
    • 85031051606 scopus 로고    scopus 로고
    • note
    • 20 to possess an energy minimum in what was termed the tweezer effect. Alternative complexed forms of n-BuLi/1,3-DMB are under current investigation.
  • 48
    • 85031056905 scopus 로고    scopus 로고
    • Often, as with the DMB's and the TMB's, a second metalation to form various amounts of a dilithio intermediate is difficult to avoid. We suggest that a metalation that affords a single lithio intermediate for such systems as one that is 'ion-multiple specific'
    • Often, as with the DMB's and the TMB's, a second metalation to form various amounts of a dilithio intermediate is difficult to avoid. We suggest that a metalation that affords a single lithio intermediate for such systems as one that is 'ion-multiple specific'.
  • 49
    • 85031054849 scopus 로고    scopus 로고
    • For the other substrates elevation of the temperature of the reaction media brought evidence of decomposition
    • For the other substrates elevation of the temperature of the reaction media brought evidence of decomposition.
  • 55
    • 85031063387 scopus 로고    scopus 로고
    • The complete disappearance of all signals was only observed for the 1,2,4-TMB system
    • The complete disappearance of all signals was only observed for the 1,2,4-TMB system.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.