메뉴 건너뛰기




Volumn 53, Issue 27, 1997, Pages 9219-9232

On the deprotonation of η6-1,3-dimethoxybenzene-Cr(CO)3 derivatives: Influence of the reaction conditions on the regioselectivity

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; RESORCINOL DERIVATIVE;

EID: 0030962159     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00620-0     Document Type: Article
Times cited : (23)

References (62)
  • 3
    • 0342578071 scopus 로고
    • Pergamon: Oxford
    • b) Semmelhack, M.F. in Comprehensive Organometallic Chemistry II, Vol. 12, Abel, E.W.; Stone, F.G.A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, pp. 979-1015;
    • (1995) , pp. 979-1015
    • Abel, E.W.1    Stone, F.G.A.2    Wilkinson, G.3
  • 4
    • 0000958965 scopus 로고
    • Liebeskind, L.S. (Ed.); JAI Press
    • c) Uemura, M. in Advances in Metal-Organic Chemistry, Vol. 2; Liebeskind, L.S. (Ed.); JAI Press, 1991, 195-267.
    • (1991) Advances in Metal-organic Chemistry , vol.2 , pp. 195-267
    • Uemura, M.1
  • 6
    • 0342578033 scopus 로고
    • Pergamon: Oxford
    • For a review, see: Semmelhack, M.F. in Comprehensive Organometallic Chemistry II, Vol. 12, Abel, E.W.; Stone, F.G.A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, pp. 1017-1038.
    • (1995) , pp. 1017-1038
    • Abel, E.W.1    Stone, F.G.A.2    Wilkinson, G.3
  • 9
    • 0342578037 scopus 로고
    • Pergamon: Oxford
    • b) Davies, S.G.; McCarthy, T.D. in Comprehensive Organometallic Chemistry II, Vol. 12, Abel, E.W.; Stone, F.G.A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, pp. 1039-1070.
    • (1995) , pp. 1039-1070
    • Abel, E.W.1    Stone, F.G.A.2    Wilkinson, G.3
  • 11
    • 33748242413 scopus 로고
    • For some recent publications in this series, see: a) Schmalz, H.-G.; Arnold, M.; Hollander, J.; Bats, J.W. Angew. Chem. 1994, 106, 77; Angew. Chem. Int. Ed. Engl. 1994, 33, 109;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 109
  • 16
    • 0029821411 scopus 로고    scopus 로고
    • e) Schmalz, H.-G.; Schellhaas, K. Angew. Chem. 1996, 108, 2277; Angew. Chem. Int. Ed. Engl.1996, 35, 2146.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2146
  • 17
  • 29
    • 0342578035 scopus 로고    scopus 로고
    • See also refs. 6 and 5c
    • c) See also refs. 6 and 5c;
  • 30
    • 0020620451 scopus 로고
    • d) An efficient, alternative synthesis employs the Grignard reagent derived from 5-chloro-1,3-dimethoxybenzene: Novák, J.; Salemink, C.A. Synthesis 1983, 597.
    • (1983) Synthesis , pp. 597
    • Novák, J.1    Salemink, C.A.2
  • 35
    • 0343883822 scopus 로고    scopus 로고
    • see also ref 10b
    • c) see also ref 10b.
  • 38
    • 0342578034 scopus 로고    scopus 로고
    • for a review, see ref 2
    • c) for a review, see ref 2,
  • 45
    • 0343012396 scopus 로고    scopus 로고
    • note
    • Only one enantiomer is depicted in the case of chiral structures which were, of course, obtained as racemic mixtures.
  • 47
    • 0343883820 scopus 로고    scopus 로고
    • note
    • 13C NMR, MS).
  • 48
    • 85047670240 scopus 로고
    • 3 complexes resulting from tele-or cine-substitution of a methoxy group, see, for instance refs. 4a, 23b as well as: a) Schmalz, H.-G.; Schellhaas, K. Tetrahedron Lett 1995, 36, 5511;
    • (1995) Tetrahedron Lett , vol.36 , pp. 5511
    • Schmalz, H.-G.1    Schellhaas, K.2
  • 51
    • 0001951894 scopus 로고    scopus 로고
    • see also ref 1b
    • c) Rose-Munch, F.; Bellot, O.; Mignon, L.; Semra, A.; Robert, F.; Jeannin, Y. J. Organomet. Chem. 1991, 402, 1; see also ref 1b.
  • 54
    • 0342578031 scopus 로고    scopus 로고
    • note
    • While the 2-regioselectivity in the ortho-metallation of 1,3-disubstituted benzene derivatives is not always complete (compare ref 10a), the highly selective formation of rac-19 is unprecedented.
  • 57
    • 0342578026 scopus 로고    scopus 로고
    • note
    • For the synthesis and data of 33, see, for instance: refs. 8c and 9c; and refs. cited therein.
  • 58
    • 0342578027 scopus 로고    scopus 로고
    • note
    • For the conversion of 33 into olivetol, see, for instance: a) ref 8c (Pyr-HCl, 82 %),
  • 59
    • 0342578028 scopus 로고    scopus 로고
    • note
    • b) ref 9a (HBr, 81 %).
  • 60
    • 0010011942 scopus 로고
    • 3 is also dependent on the reaction conditions (kinetic versus thermodynamic control), see: a) Treichel, P.M.; Kirss, R.U. Organometallics 1987, 6, 249;
    • (1987) Organometallics , vol.6 , pp. 249
    • Treichel, P.M.1    Kirss, R.U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.