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Volumn 617-618, Issue , 2001, Pages 261-268

Intramolecular carbon-carbon coupling reactions of a κ2(P,P)-bis(diphenylphosphino)methanide ligand with unsaturated carbene moieties in indenyl-ruthenium(II) complexes

Author keywords

Alkenyl complexes; C C couplings; Indenyl; Ruthenium; Vinylidene complexes; , Unsaturated carbene complexes

Indexed keywords


EID: 0001787734     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00497-6     Document Type: Article
Times cited : (11)

References (46)
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    • For comprehensive reviews see: (a) M.I. Bruce, A.G. Swincer, Adv. Organomet. Chem. 22 (1983) 59. (b) A.B. Antonova, A.A. Johansson, Russ. Chem. Rev. 58 (1989) 693. (c) M.I. Bruce, Chem. Rev. 91 (1991) 197. (d) H. Werner, Nachr. Chem. Tech. Lab. 40 (1992) 435. (e) H. Werner, J. Organomet. Chem. 475 (1994) 44. (f) M.C. Puerta, P. Valerga, Coord. Chem. Rev. 193-195 (1999) 977.
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    • Representative examples are reported in: (a) P. Schwab, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc. 118 (1996) 100. (b) H. Katayama, F. Ozawa, Chem. Lett. (1998) 67. (c) H. Katayama, T. Yoshida, F. Ozawa, J. Organomet. Chem. 562 (1998) 203. (d) I. del Rio, G. van Koten, Tetrahedron Lett. 40 (1999) 1401.
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    • Representative examples are reported in: (a) P. Schwab, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc. 118 (1996) 100. (b) H. Katayama, F. Ozawa, Chem. Lett. (1998) 67. (c) H. Katayama, T. Yoshida, F. Ozawa, J. Organomet. Chem. 562 (1998) 203. (d) I. del Rio, G. van Koten, Tetrahedron Lett. 40 (1999) 1401.
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    • Representative examples are reported in: (a) P. Schwab, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc. 118 (1996) 100. (b) H. Katayama, F. Ozawa, Chem. Lett. (1998) 67. (c) H. Katayama, T. Yoshida, F. Ozawa, J. Organomet. Chem. 562 (1998) 203. (d) I. del Rio, G. van Koten, Tetrahedron Lett. 40 (1999) 1401.
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    • Katayama, H.1    Yoshida, T.2    Ozawa, F.3
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    • (d)
    • Representative examples are reported in: (a) P. Schwab, R.H. Grubbs, J.W. Ziller, J. Am. Chem. Soc. 118 (1996) 100. (b) H. Katayama, F. Ozawa, Chem. Lett. (1998) 67. (c) H. Katayama, T. Yoshida, F. Ozawa, J. Organomet. Chem. 562 (1998) 203. (d) I. del Rio, G. van Koten, Tetrahedron Lett. 40 (1999) 1401.
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    • See for example: (a)
    • See for example: (a) B.E.R. Schilling, R. Hoffmann, D.L. Lichtenberger, J. Am. Chem. Soc. 101 (1979) 585. (b) N.M. Kostic, R.F. Fenske, Organometallics 1 (1982) 974. (c) M.P. Gamasa, J. Gimeno, B. Martín-Vaca, J. Borge, E. Pérez-Carreño, S. García-Granda, Organometallics 13 (1994) 4045.
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    • See for example: (a) B.E.R. Schilling, R. Hoffmann, D.L. Lichtenberger, J. Am. Chem. Soc. 101 (1979) 585. (b) N.M. Kostic, R.F. Fenske, Organometallics 1 (1982) 974. (c) M.P. Gamasa, J. Gimeno, B. Martín-Vaca, J. Borge, E. Pérez-Carreño, S. García-Granda, Organometallics 13 (1994) 4045.
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    • (a) Formation of related 1-metalla-2,5-diphosphabicyclo[2.1.1]hexane rings (M=Fe, Ru) as the result of an intramolecular coupling between a deprotonated dppe (1,2-bis(diphenylphosphino)ethane) ligand and a vinylidene moiety has been also described:
    • (a) M.P. Gamasa, J. Gimeno, E. Lastra, B.M. Martín, A. Aguirre, S. García-Granda, P. Pertierra, J. Organomet. Chem. 429 (1992) C19. Formation of related 1-metalla-2,5-diphosphabicyclo[2.1.1]hexane rings (M=Fe, Ru) as the result of an intramolecular coupling between a deprotonated dppe (1,2-bis(diphenylphosphino)ethane) ligand and a vinylidene moiety has been also described:
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    • Gamasa, M.P.1    Gimeno, J.2    Lastra, E.3    Martín, B.M.4    Aguirre, A.5    García-Granda, S.6    Pertierra, P.7
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    • For a review on the chemistry of alkenyl complexes see
    • For a review on the chemistry of alkenyl complexes see: D.L. Reger, Acc. Chem. Res. 21 (1988) 229.
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    • 3) on the β-carbon of complexes 6, in order to generate cationic carbenic species, were unsuccessful obtaining instead complicated mixtures of uncharacterized products.
    • 3) on the β-carbon of complexes 6, in order to generate cationic carbenic species, were unsuccessful obtaining instead complicated mixtures of uncharacterized products.
  • 36
    • 0040012647 scopus 로고
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) in: A. de Meijere, H.T. Dieck, (Eds.) Springer-Verlag, Berlin
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1987) Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field
    • Dötz, K.H.1
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    • 0000533326 scopus 로고
    • (b) in: B.M. Trost, I. Fleming (Eds.) Pergamon, New York
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1065
    • Wulff, W.D.1
  • 38
    • 0000413316 scopus 로고
    • (c)
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1990) Pure Appl. Chem. , vol.62 , pp. 691
    • Hegedus, L.S.1
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    • (d) in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.) Pergamon, Oxford
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1995) Comprehensive Organometallic Chemistry II , vol.5 , pp. 155
    • Winter, M.J.1
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    • (e) in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.) Pergamon, Oxford
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 389
    • Doyle, M.P.1
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    • 0000134377 scopus 로고
    • (f) in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.) Pergamon, Oxford
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 469
    • Wulff, W.D.1
  • 42
    • 0000951659 scopus 로고
    • (g) in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.) Oxford
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1995) Comprehensive Organometallic Chemistry II, Pergamon , vol.12 , pp. 549
    • Hegedus, L.S.1
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    • 0000156844 scopus 로고    scopus 로고
    • (h)
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 543
    • Barluenga, J.1
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    • (i) Wiley-VCH, Weinheim
    • 4 have shown a wide and versatile reactivity playing a burgeoning role in modern organic synthesis. For reviews see: (a) K.H. Dötz, in: A. de Meijere, H.T. Dieck, (Eds.), Organometallics in Organic Synthesis 1: Aspects of a Modern Interdisciplinary Field, Springer-Verlag, Berlin, 1987. (b) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 5, Pergamon, New York, 1991, p. 1065. (c) L.S. Hegedus, Pure Appl. Chem. 62 (1990) 691. (d) M.J. Winter, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 5, Pergamon, Oxford, 1995, p. 155. (e) M.P. Doyle, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 389. (f) W.D. Wulff, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, 1995, p. 469. (g) L.S. Hegedus, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, Pergamon, vol. 12, Oxford, 1995, p. 549. (h) J. Barluenga, Pure Appl. Chem. 68 (1996) 543. (i) F. Zaragoza Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
    • (1999) Metal Carbenes in Organic Synthesis
    • Zaragoza Dörwald, F.1
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    • The thermodynamic stability of a six-membered ring towards a four-membered ring could be also responsible of the observed regioselectivity
    • The thermodynamic stability of a six-membered ring towards a four-membered ring could be also responsible of the observed regioselectivity.


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