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Volumn , Issue 12, 1998, Pages 1883-1905

Highly Regioselective Benzylic Deprotonation of Some (η6-Tetralin)- and (η6-tras-Octahydroanthracene)Cr(CO)3 Derivatives: Is the Regioselectivity Stereoelectronically Controlled?

Author keywords

(Arene)tricarbonylchromium complexes; Arene complexes; Benzylic deprotonation; Chromium; Conformational analysis; Stereoelectronic effects; Stereoselective synthesis

Indexed keywords

ATOMS; CHROMIUM COMPOUNDS; CONFORMATIONS; CRYSTAL ATOMIC STRUCTURE; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 0003163759     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(199812)1998:12<1883::aid-ejic1883>3.0.co;2-%23     Document Type: Article
Times cited : (14)

References (120)
  • 1
    • 0000747080 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford
    • For some selected recent reviews, see: [1a] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 979-1015. [1b] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1017-1038. [1c] S. G. Davies, T. D. McCarthy in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1039-1070. [1d] L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994, chapter 10.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 979-1015
    • Semmelhack, M.F.1
  • 2
    • 0000747083 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford
    • For some selected recent reviews, see: [1a] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 979-1015. [1b] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1017-1038. [1c] S. G. Davies, T. D. McCarthy in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1039-1070. [1d] L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994, chapter 10.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 1017-1038
    • Semmelhack, M.F.1
  • 3
    • 0000747080 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford
    • For some selected recent reviews, see: [1a] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 979-1015. [1b] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1017-1038. [1c] S. G. Davies, T. D. McCarthy in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1039-1070. [1d] L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994, chapter 10.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 1039-1070
    • Davies, S.G.1    McCarthy, T.D.2
  • 4
    • 0003923046 scopus 로고
    • University Science Books, Mill Valley, chapter 10
    • For some selected recent reviews, see: [1a] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 979-1015. [1b] M. F. Semmelhack in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1017-1038. [1c] S. G. Davies, T. D. McCarthy in Comprehensive Organometallic Chemistry II, vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 1039-1070. [1d] L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994, chapter 10.
    • (1994) Transition Metals in the Synthesis of Complex Organic Molecules
    • Hegedus, L.S.1
  • 12
    • 33748242413 scopus 로고
    • H.-G. Schmalz, M. Arnold, J. Hollander, G. Dürner, 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
    • H.-G. Schmalz, K. Schellhaas, Angew. Chem. 1996, 108, 2277; Angew. Chem. Int Ed Engl. 1996, 35, 2146.
    • (1996) Angew. Chem. Int Ed Engl. , vol.35 , pp. 2146
  • 19
    • 0000674378 scopus 로고
    • 3 complexes, there is a para-directing effect of electron-withdrawing groups and a meia-directing effect of donor substituents. See, for example: [6a] G. Jaouen, S. Top, A. Laconi, D. Couturier, J. Brocard, J. Am. Chem. Soc. 1984, 106, 2207. [6b] J. Brocard, A. Laconi, D. Couturier, S. Top, G. Jaouen, J. Chem. Soc., Chem. Commun. 1984, 475. [6c] J. Brocard, L. Pelinski, J. Lebibi, J Organomet. Chem. 1986, 309, 299. [6d] J. Brocard, J. Lebibi, J. Organomet. Chem. 1987, 320, 295. [6e] J. Lebibi, L. Pelinski, J. Brocard, Tetrahedron 1990, 46, 6011.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 2207
    • Jaouen, G.1    Top, S.2    Laconi, A.3    Couturier, D.4    Brocard, J.5
  • 20
    • 37049109172 scopus 로고
    • 3 complexes, there is a para-directing effect of electron-withdrawing groups and a meia-directing effect of donor substituents. See, for example: [6a] G. Jaouen, S. Top, A. Laconi, D. Couturier, J. Brocard, J. Am. Chem. Soc. 1984, 106, 2207. [6b] J. Brocard, A. Laconi, D. Couturier, S. Top, G. Jaouen, J. Chem. Soc., Chem. Commun. 1984, 475. [6c] J. Brocard, L. Pelinski, J. Lebibi, J Organomet. Chem. 1986, 309, 299. [6d] J. Brocard, J. Lebibi, J. Organomet. Chem. 1987, 320, 295. [6e] J. Lebibi, L. Pelinski, J. Brocard, Tetrahedron 1990, 46, 6011.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 475
    • Brocard, J.1    Laconi, A.2    Couturier, D.3    Top, S.4    Jaouen, G.5
  • 21
    • 0010935208 scopus 로고
    • 3 complexes, there is a para-directing effect of electron-withdrawing groups and a meia-directing effect of donor substituents. See, for example: [6a] G. Jaouen, S. Top, A. Laconi, D. Couturier, J. Brocard, J. Am. Chem. Soc. 1984, 106, 2207. [6b] J. Brocard, A. Laconi, D. Couturier, S. Top, G. Jaouen, J. Chem. Soc., Chem. Commun. 1984, 475. [6c] J. Brocard, L. Pelinski, J. Lebibi, J Organomet. Chem. 1986, 309, 299. [6d] J. Brocard, J. Lebibi, J. Organomet. Chem. 1987, 320, 295. [6e] J. Lebibi, L. Pelinski, J. Brocard, Tetrahedron 1990, 46, 6011.
    • (1986) J Organomet. Chem. , vol.309 , pp. 299
    • Brocard, J.1    Pelinski, L.2    Lebibi, J.3
  • 22
    • 0011352339 scopus 로고
    • 3 complexes, there is a para-directing effect of electron-withdrawing groups and a meia-directing effect of donor substituents. See, for example: [6a] G. Jaouen, S. Top, A. Laconi, D. Couturier, J. Brocard, J. Am. Chem. Soc. 1984, 106, 2207. [6b] J. Brocard, A. Laconi, D. Couturier, S. Top, G. Jaouen, J. Chem. Soc., Chem. Commun. 1984, 475. [6c] J. Brocard, L. Pelinski, J. Lebibi, J Organomet. Chem. 1986, 309, 299. [6d] J. Brocard, J. Lebibi, J. Organomet. Chem. 1987, 320, 295. [6e] J. Lebibi, L. Pelinski, J. Brocard, Tetrahedron 1990, 46, 6011.
    • (1987) J. Organomet. Chem. , vol.320 , pp. 295
    • Brocard, J.1    Lebibi, J.2
  • 23
    • 0042478256 scopus 로고
    • 3 complexes, there is a para-directing effect of electron-withdrawing groups and a meia-directing effect of donor substituents. See, for example: [6a] G. Jaouen, S. Top, A. Laconi, D. Couturier, J. Brocard, J. Am. Chem. Soc. 1984, 106, 2207. [6b] J. Brocard, A. Laconi, D. Couturier, S. Top, G. Jaouen, J. Chem. Soc., Chem. Commun. 1984, 475. [6c] J. Brocard, L. Pelinski, J. Lebibi, J Organomet. Chem. 1986, 309, 299. [6d] J. Brocard, J. Lebibi, J. Organomet. Chem. 1987, 320, 295. [6e] J. Lebibi, L. Pelinski, J. Brocard, Tetrahedron 1990, 46, 6011.
    • (1990) Tetrahedron , vol.46 , pp. 6011
    • Lebibi, J.1    Pelinski, L.2    Brocard, J.3
  • 25
    • 2042487195 scopus 로고
    • J. Blagg, S. G. Davies, C. L. Goodfellow, K. H. Sutton, J. Chem. Soc., Perkin Trans, I 1987, 1805. The term "complex-induced proximity effect" was coined by Beak and Meyers: P. Beak, A. I. Meyers, Ace. Chem. Res. 1986, 19, 356.
    • (1986) Ace. Chem. Res. , vol.19 , pp. 356
    • Beak, P.1    Meyers, A.I.2
  • 26
    • 0003536850 scopus 로고
    • Pergamon, Oxford, and references cited therein
    • The lithiated species can be assumed to possess a structure 3, in which the deprotonated center is part of a newly formed double bond (see refs.[1c][2]). In analogy to the deprotonation of ketones, the C-H bond to be broken during the deprotonation step should, for stereoelectronic reasons, be as close to parallel as possible in relation to the aryl π orbitals, so that the developing p orbital can be stabuzed early. For related discussions, see, for instance: [8a] P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, Oxford, 1983, pp. 243-267. and references cited therein. [8b] K. Seemeyer, R. H. Hertwig, J. Hrusák, W. Koch, H. Schwarz, Organometallics 1995, 14, 4409.
    • (1983) Stereoelectronic Effects in Organic Chemistry , pp. 243-267
    • Deslongchamps, P.1
  • 27
    • 0011414038 scopus 로고
    • The lithiated species can be assumed to possess a structure 3, in which the deprotonated center is part of a newly formed double bond (see refs.[1c][2]). In analogy to the deprotonation of ketones, the C-H bond to be broken during the deprotonation step should, for stereoelectronic reasons, be as close to parallel as possible in relation to the aryl π orbitals, so that the developing p orbital can be stabuzed early. For related discussions, see, for instance: [8a] P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, Oxford, 1983, pp. 243-267. and references cited therein. [8b] K. Seemeyer, R. H. Hertwig, J. Hrusák, W. Koch, H. Schwarz, Organometallics 1995, 14, 4409.
    • (1995) Organometallics , vol.14 , pp. 4409
    • Seemeyer, K.1    Hertwig, R.H.2    Hrusák, J.3    Koch, W.4    Schwarz, H.5
  • 31
    • 33947296831 scopus 로고
    • For Diels-Alder reactions of intermediate o-quinodimethanes, see: [10a] I. L. Klundt, Chem Rev. 1970, 70, 471. [10b] W. Oppolzer, Synthesis, 1978, 793. [10c] T. Tuschka, K. Naito, B. Rickborn, J. Org. Chem 1983, 48, 70 and references cited therein.
    • (1970) Chem Rev. , vol.70 , pp. 471
    • Klundt, I.L.1
  • 32
    • 85065852858 scopus 로고
    • For Diels-Alder reactions of intermediate o-quinodimethanes, see: [10a] I. L. Klundt, Chem Rev. 1970, 70, 471. [10b] W. Oppolzer, Synthesis, 1978, 793. [10c] T. Tuschka, K. Naito, B. Rickborn, J. Org. Chem 1983, 48, 70 and references cited therein.
    • (1978) Synthesis , pp. 793
    • Oppolzer, W.1
  • 33
    • 0002713075 scopus 로고
    • and references cited therein
    • For Diels-Alder reactions of intermediate o-quinodimethanes, see: [10a] I. L. Klundt, Chem Rev. 1970, 70, 471. [10b] W. Oppolzer, Synthesis, 1978, 793. [10c] T. Tuschka, K. Naito, B. Rickborn, J. Org. Chem 1983, 48, 70 and references cited therein.
    • (1983) J. Org. Chem , vol.48 , pp. 70
    • Tuschka, T.1    Naito, K.2    Rickborn, B.3
  • 35
    • 26144448611 scopus 로고
    • Compound rac-13 can also be obtained as a mixture by partial hydrogenation of anthracene: [11b] R. Köster, M. Yalpani, Chem. Ber. 1990, 123, 719. [11c] J. Eloranta, Finn Chem. Lett. 1974, 112.
    • (1990) Chem. Ber. , vol.123 , pp. 719
    • Köster, R.1    Yalpani, M.2
  • 36
    • 85163235268 scopus 로고
    • Compound rac-13 can also be obtained as a mixture by partial hydrogenation of anthracene: [11b] R. Köster, M. Yalpani, Chem. Ber. 1990, 123, 719. [11c] J. Eloranta, Finn Chem. Lett. 1974, 112.
    • (1974) Finn Chem. Lett. , pp. 112
    • Eloranta, J.1
  • 47
    • 85163229575 scopus 로고    scopus 로고
    • note
    • It should be noted that mild conditions (0°C) are required to achieve a reasonably high yield. At higher temperatures, an increased formation of by-products was observed and the isolated yield of rac-20 dropped, for instance, to 32% when the reaction was performed at 40°C. Addition of HMPA, which is reported to give improved yields in some comparable cases[15], resulted only in a decreased yield of rac-20 (ca. 30% at 0°C).
  • 51
    • 0001168999 scopus 로고
    • For some early examples for the use of dimenthyl fumarate in asymmetric Diels-Alder reactions, see: [20a] H. M. Walborsky, L. Barash, T. C. Davis, J. Org. Chem. 1961, 26, 4778. [20b] H. M Walborsky, L. Barash, T. C. Davis, Tetrahedron 1963, 19, 2333. [20c] J. Sauer, J. Kredel, Angew. Chem. 1965, 77, 1037. [20d] J. Sauer, J. Kredel, Tetrahedron 1966, 22, 6359.
    • (1961) J. Org. Chem. , vol.26 , pp. 4778
    • Walborsky, H.M.1    Barash, L.2    Davis, T.C.3
  • 52
    • 33748888324 scopus 로고
    • For some early examples for the use of dimenthyl fumarate in asymmetric Diels-Alder reactions, see: [20a] H. M. Walborsky, L. Barash, T. C. Davis, J. Org. Chem. 1961, 26, 4778. [20b] H. M Walborsky, L. Barash, T. C. Davis, Tetrahedron 1963, 19, 2333. [20c] J. Sauer, J. Kredel, Angew. Chem. 1965, 77, 1037. [20d] J. Sauer, J. Kredel, Tetrahedron 1966, 22, 6359.
    • (1963) Tetrahedron , vol.19 , pp. 2333
    • Walborsky, H.M.1    Barash, L.2    Davis, T.C.3
  • 53
    • 0345265187 scopus 로고
    • For some early examples for the use of dimenthyl fumarate in asymmetric Diels-Alder reactions, see: [20a] H. M. Walborsky, L. Barash, T. C. Davis, J. Org. Chem. 1961, 26, 4778. [20b] H. M Walborsky, L. Barash, T. C. Davis, Tetrahedron 1963, 19, 2333. [20c] J. Sauer, J. Kredel, Angew. Chem. 1965, 77, 1037. [20d] J. Sauer, J. Kredel, Tetrahedron 1966, 22, 6359.
    • (1965) Angew. Chem. , vol.77 , pp. 1037
    • Sauer, J.1    Kredel, J.2
  • 54
    • 0001265923 scopus 로고
    • For some early examples for the use of dimenthyl fumarate in asymmetric Diels-Alder reactions, see: [20a] H. M. Walborsky, L. Barash, T. C. Davis, J. Org. Chem. 1961, 26, 4778. [20b] H. M Walborsky, L. Barash, T. C. Davis, Tetrahedron 1963, 19, 2333. [20c] J. Sauer, J. Kredel, Angew. Chem. 1965, 77, 1037. [20d] J. Sauer, J. Kredel, Tetrahedron 1966, 22, 6359.
    • (1966) Tetrahedron , vol.22 , pp. 6359
    • Sauer, J.1    Kredel, J.2
  • 57
    • 85163234370 scopus 로고    scopus 로고
    • -1, λ = 254 nm, retention time for 21: 15.54 min; retention time for ent21: 14.10 min.
    • -1, λ = 254 nm, retention time for 21: 15.54 min; retention time for ent21: 14.10 min.
  • 60
    • 0000315424 scopus 로고
    • (Eds.: B. M. Trost, T. Fleming), Pergamon, Oxford
    • For some reviews on radical cyclizations, see: [24a] D. P. Curran, in Comprehensive Organic Synthesis, vol. 4 (Eds.: B. M. Trost, T. Fleming), Pergamon, Oxford, 1991, pp. 779-831. [24b] C. P. Jasperse, D. P. Curran, T. L. Fervig, Chem. Rev. 1991, 91, 1237.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 779-831
    • Curran, D.P.1
  • 61
    • 0000702878 scopus 로고
    • For some reviews on radical cyclizations, see: [24a] D. P. Curran, in Comprehensive Organic Synthesis, vol. 4 (Eds.: B. M. Trost, T. Fleming), Pergamon, Oxford, 1991, pp. 779-831. [24b] C. P. Jasperse, D. P. Curran, T. L. Fervig, Chem. Rev. 1991, 91, 1237.
    • (1991) Chem. Rev. , vol.91 , pp. 1237
    • Jasperse, C.P.1    Curran, D.P.2    Fervig, T.L.3
  • 62
    • 85163227414 scopus 로고    scopus 로고
    • note
    • In our hands, the yield of rac-13 was only 29% (ref.[12]: 79%) after chromatography and recrystallization. The melting point of the our material (64°C), however, was found to exceed that given in the literature (53°C)[12].
  • 67
    • 85163233180 scopus 로고    scopus 로고
    • note
    • -3.
  • 68
    • 85163223413 scopus 로고    scopus 로고
    • note
    • -3.
  • 69
    • 85163235476 scopus 로고    scopus 로고
    • note
    • -3.
  • 70
    • 85163228405 scopus 로고    scopus 로고
    • note
    • -3. -Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101004. Copies of the data can be obtained free of charge on application to CCDC. 12 Union Road, Cambridge CB2 1EZ. UK [Fax: int. code + 44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
  • 72
    • 85163231028 scopus 로고    scopus 로고
    • unpublished results
    • Complex rac-1 was prepared as described in ref.[5]; complex 50 was obtained from 6,7-dimethoxytetralin by complexation and disilylation: H.-G. Schmalz, A. Schwarz, unpublished results.
    • Schmalz, H.-G.1    Schwarz, A.2
  • 73
    • 85163224433 scopus 로고    scopus 로고
    • note
    • 6]DMSO conditions (lower temperatures and/or shorter reaction times) failed.
  • 74
    • 85163228697 scopus 로고    scopus 로고
    • note
    • The degree of deuteration (and the level of inaccuracy) was determined (estimated) by comparison with the integrals observed for the methoxy or the TMS groups.
  • 75
    • 85163228430 scopus 로고    scopus 로고
    • note
    • The fact that no significant loss of regioselectivity was found in these experiments indicates that the inherent directing effect must be stronger than the primary kinetic isotope effect.
  • 76
    • 85163234379 scopus 로고    scopus 로고
    • note
    • A protonation at the chromium atom of the anionic intermediate, which would eventually have resulted in the formation of an endo-protonated complex could thereby be excluded.
  • 77
    • 85163233163 scopus 로고    scopus 로고
    • note
    • -3. Further details of the crystal structure investigations are available on request from the CCDC; for details see ref. [29d].
  • 78
    • 85163228336 scopus 로고    scopus 로고
    • note
    • The formation of benzylic alkylation products derived from rac-7 was established by NMR of the crude product mixture but purification was not successful due to rapid decomposition.
  • 79
    • 85163224289 scopus 로고    scopus 로고
    • note
    • Brocard and Lebibi (ref.[6d]) summarize their experiments: "The regiospecificity of the benzylic functional group of arenetricarbonylchromium cannot be explained by preferential attack at the carbon which is eclipsed by the chromium-carbonyl bond. Electronic effects in directing the regiospecificity of benzylic attack were found to predominate."
  • 98
    • 85163228641 scopus 로고    scopus 로고
    • This representation is favorable due to the experimental fact that the anions possess a high configurative stability; see, for instance: S. E. Gibson, M. J. Schneider, M. H. Smith, J. Chem Soc., Chem. Commun. 1996, 839. Our own NMR data of some lithiated species (see: T. Volk, Dissertation, TU Berlin, 1996) support this picture.
    • (1996) J. Chem Soc., Chem. Commun. , vol.839
    • Gibson, S.E.1    Schneider, M.J.2    Smith, M.H.3
  • 99
    • 85163224507 scopus 로고    scopus 로고
    • Dissertation, TU Berlin
    • This representation is favorable due to the experimental fact that the anions possess a high configurative stability; see, for instance: S. E. Gibson, M. J. Schneider, M. H. Smith, J. Chem Soc., Chem. Commun. 1996, 839. Our own NMR data of some lithiated species (see: T. Volk, Dissertation, TU Berlin, 1996) support this picture.
    • (1996)
    • Volk, T.1
  • 100
    • 33847089848 scopus 로고
    • 3Si) and that the arene ligand carbon atoms which are eclipsed with a CO ligand are predicted to be more electrophilic (see: refs. [1a][40][41], as well as: T. A. Albright, P. Hofmann, R. Hoffmann, J. Am. Chem. Soc. 1977, 99, 7546).
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 7546
    • Albright, T.A.1    Hofmann, P.2    Hoffmann, R.3
  • 101
    • 0007252545 scopus 로고
    • -1 in the case of highly substituted systems. For a review, see: [47a] M. J. McGlinchey, Adv. Organomet. Chem. 1992, 34, 285. See also: [47b] K. V. Kilway, J. S. Siegel, J. Am. Chem. Soc 1992, 114, 255; and references cited therein.
    • (1992) Adv. Organomet. Chem. , vol.34 , pp. 285
    • McGlinchey, M.J.1
  • 102
    • 0000800611 scopus 로고
    • and references cited therein
    • -1 in the case of highly substituted systems. For a review, see: [47a] M. J. McGlinchey, Adv. Organomet. Chem. 1992, 34, 285. See also: [47b] K. V. Kilway, J. S. Siegel, J. Am. Chem. Soc 1992, 114, 255; and references cited therein.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 255
    • Kilway, K.V.1    Siegel, J.S.2
  • 106
    • 0010775171 scopus 로고    scopus 로고
    • R. A. Henderson, Angew. Chem. 1996, 108, 1024; Angew. Chem. Int. Ed. Engl. 1996, 35, 946.
    • (1996) Angew. Chem. , vol.108 , pp. 1024
    • Henderson, R.A.1
  • 107
    • 0029791424 scopus 로고    scopus 로고
    • R. A. Henderson, Angew. Chem. 1996, 108, 1024; Angew. Chem. Int. Ed. Engl. 1996, 35, 946.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 946
  • 108
    • 85163228349 scopus 로고    scopus 로고
    • note
    • 6.
  • 109
    • 85163229440 scopus 로고    scopus 로고
    • note
    • After decomplexation, the isomers could be unambiguously assigned by NOE experiments (see Experimental Section).
  • 114
    • 33748638673 scopus 로고
    • and refs. cited therein
    • H.-G. Schmalz; B. Millies, J. W. Bats, G. Dürner, Angew. Chem. 1992, 104, 640; Angew. Chem. Int Ed. Engl. 1992, 31, 631; and refs. cited therein.
    • (1992) Angew. Chem. Int Ed. Engl. , vol.31 , pp. 631
  • 119
    • 85163227129 scopus 로고    scopus 로고
    • For the assignments of the benzylic protons, see Table 2
    • For the assignments of the benzylic protons, see Table 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.