메뉴 건너뛰기




Volumn 24, Issue 1, 2005, Pages 103-109

Inhibiting δ → π Isomerization of Aryloxide Ligands in Late Transition-Metal Complexes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHELATION; CHEMICAL BONDS; COMPLEXATION; CRYSTAL STRUCTURE; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE;

EID: 12344304487     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049394j     Document Type: Article
Times cited : (23)

References (57)
  • 11
    • 37049100966 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1976) J. Chem. Soc., Dalton Trans. , pp. 1995
    • Cole-Hamilton, D.J.1    Young, R.J.2    Wilkinson, G.3
  • 12
    • 37049102370 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1979) J. Chem. Soc., Dalton Trans. , pp. 1618
    • Rosete, R.O.1    Cole-Hamilton, D.J.2    Wilkinson, G.3
  • 13
    • 0000211535 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1994) Inorg. Chem. , vol.33 , pp. 5316
    • Christ, M.L.1    Sabo-Etienne, S.2    Chung, G.3    Chaudret, B.4
  • 14
    • 0000212112 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1977) New J. Chem. , vol.1 , pp. 141
    • Cole-Hamilton, D.J.1    Wilkinson, G.2
  • 15
    • 0001784621 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1979) J. Organomet. Chem. , vol.175 , pp. 87
    • Bennett, M.A.1    Matheson, T.W.2
  • 16
    • 0013362133 scopus 로고    scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1996) Organometallics , vol.15 , pp. 3095
    • Bücken, K.1    Koelle, U.2    Pasch, R.3    Ganter, B.4
  • 17
    • 37049084997 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 1844
    • Chaudret, B.1    Xiaodong, H.2    Huang, Y.3
  • 18
    • 33751499130 scopus 로고
    • 4. See: (a) Cole-Hamilton, D. J.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 1995. (b) Rosete, R. O.; Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1979, 1618. (c) Christ, M. L.; Sabo-Etienne, S.; Chung, G.; Chaudret, B. Inorg. Chem. 1994, 33, 5316. (d) Cole-Hamilton, D. J.; Wilkinson, G. New J. Chem. 1977, 1, 141. (e) Bennett, M. A.; Matheson, T. W. J. Organomet. Chem. 1979, 175, 87. (f) Bücken, K.; Koelle, U.; Pasch, R.; Ganter, B. Organometallics 1996, 15, 3095. (g) Chaudret, B.; Xiaodong, H.; Huang, Y. J. Chem. Soc., Chem. Commun. 1989, 1844. (h) Koelle, U.; Wang, M. H.; Raabe, G. Organometallics 1991, 10, 2573.
    • (1991) Organometallics , vol.10 , pp. 2573
    • Koelle, U.1    Wang, M.H.2    Raabe, G.3
  • 20
    • 0037861768 scopus 로고    scopus 로고
    • While of limited utility for olefin metathesis, such π-aryloxide species are of interest as catalysts for asymmetric Diels-Alder reactions (see: Faller, J. W.; D'Alliessi, D. G. Organometallics 2003, 22, 2749. F aller, J. W. ; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662) and are of potential relevance for nucleophilic phenol functionalization (see: Le Bras, J. ; Amouri, H.; Vaissermann, J. Inorg. Chem. 1998, 37, 5066 and references therein) or carbonylation (see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179).
    • (2003) Organometallics , vol.22 , pp. 2749
    • Faller, J.W.1    D'Alliessi, D.G.2
  • 21
    • 0001746825 scopus 로고    scopus 로고
    • While of limited utility for olefin metathesis, such π-aryloxide species are of interest as catalysts for asymmetric Diels-Alder reactions (see: Faller, J. W.; D'Alliessi, D. G. Organometallics 2003, 22, 2749. F aller, J. W. ; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662) and are of potential relevance for nucleophilic phenol functionalization (see: Le Bras, J. ; Amouri, H.; Vaissermann, J. Inorg. Chem. 1998, 37, 5066 and references therein) or carbonylation (see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179).
    • (2002) Organometallics , vol.21 , pp. 1662
    • Faller, J.W.1    Lavoie, A.R.2    Grimmond, B.J.3
  • 22
    • 12344324309 scopus 로고    scopus 로고
    • While of limited utility for olefin metathesis, such π-aryloxide species are of interest as catalysts for asymmetric Diels-Alder reactions (see: Faller, J. W.; D'Alliessi, D. G. Organometallics 2003, 22, 2749. F aller, J. W. ; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662) and are of potential relevance for nucleophilic phenol functionalization (see: Le Bras, J. ; Amouri, H.; Vaissermann, J. Inorg. Chem. 1998, 37, 5066 and references therein) or carbonylation (see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179).
    • (1998) Inorg. Chem. , vol.37 , pp. 5066
    • Le Bras, J.1    Amouri, H.2    Vaissermann, J.3
  • 23
    • 0029890191 scopus 로고    scopus 로고
    • While of limited utility for olefin metathesis, such π-aryloxide species are of interest as catalysts for asymmetric Diels-Alder reactions (see: Faller, J. W.; D'Alliessi, D. G. Organometallics 2003, 22, 2749. F aller, J. W. ; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662) and are of potential relevance for nucleophilic phenol functionalization (see: Le Bras, J. ; Amouri, H.; Vaissermann, J. Inorg. Chem. 1998, 37, 5066 and references therein) or carbonylation (see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179).
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4846
    • Dockter, D.W.1    Fanwick, P.E.2    Kubiak, C.P.3
  • 24
    • 0001537258 scopus 로고
    • While of limited utility for olefin metathesis, such π-aryloxide species are of interest as catalysts for asymmetric Diels-Alder reactions (see: Faller, J. W.; D'Alliessi, D. G. Organometallics 2003, 22, 2749. F aller, J. W. ; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662) and are of potential relevance for nucleophilic phenol functionalization (see: Le Bras, J. ; Amouri, H.; Vaissermann, J. Inorg. Chem. 1998, 37, 5066 and references therein) or carbonylation (see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179).
    • (1985) Organometallics , vol.4 , pp. 2179
    • Rees, W.M.1    Churchill, M.R.2    Fettinger, J.C.3    Atwood, J.D.4
  • 25
    • 0010997164 scopus 로고
    • Examples of π-bound fluorophenoxide have, however, been reported. See: (a) Koelle, U.; Hörnig, A.; Englert, U. Organometallics 1994, 13, 4064. (b) Curnow, O. J.; Hughes, R. P. J. Am. Chem. Soc. 1992, 114, 5895.
    • (1994) Organometallics , vol.13 , pp. 4064
    • Koelle, U.1    Hörnig, A.2    Englert, U.3
  • 26
    • 0038738397 scopus 로고
    • Examples of π-bound fluorophenoxide have, however, been reported. See: (a) Koelle, U.; Hörnig, A.; Englert, U. Organometallics 1994, 13, 4064. (b) Curnow, O. J.; Hughes, R. P. J. Am. Chem. Soc. 1992, 114, 5895.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5895
    • Curnow, O.J.1    Hughes, R.P.2
  • 27
    • 0346739186 scopus 로고
    • + salts in halide substitution of metal complexes has been attributed to electrophilic "pull" by the heavy-metal cations, possibly via direct electrophilic attack on the halogen atom. See: Danopoulos, A. A.; Wilkinson, G.; Sweet, T. K. N.; Hursthouse, M. B. Polyhedron 1994, 13, 2899.
    • (1994) Polyhedron , vol.13 , pp. 2899
    • Danopoulos, A.A.1    Wilkinson, G.2    Sweet, T.K.N.3    Hursthouse, M.B.4
  • 28
    • 12344304796 scopus 로고    scopus 로고
    • note
    • 1H) NMR spectrum.
  • 29
    • 12344332056 scopus 로고    scopus 로고
    • note
    • ,3 are cited relative to trifluoroacetic acid at 0 ppm.
  • 46
    • 12344264375 scopus 로고    scopus 로고
    • note
    • HC correlations revealed in HMBC experiments. For further details, see the Supporting Information.
  • 47
    • 12344332057 scopus 로고    scopus 로고
    • note
    • 31P NMR signals is made on the basis of the coupling of the O-MOP phosphorus to H3' and H4'.
  • 48
    • 12344333139 scopus 로고    scopus 로고
    • note
    • This geometry permits an incipient interaction between the oxygen and phosphorus O-MOP substituents, a feature that may account for the diastereomeric bias in formation of 7b (vide infra).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.