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Volumn , Issue 12, 2003, Pages 2225-2228

Effective and inexpensive acrylonitrile cross-metathesis: Utilisation of Grubbs II precatalyst in the presence of copper(I) chloride

(2) Rivard, Michael a Blechert, Siegfried a

a TECHNISCHE UNIVERSITÄT BERLIN (Germany)

Author keywords

Copper; Metathesis; Ruthenium; Synthetic methods

Indexed keywords

ACRYLONITRILE; COPPER CHLORIDE; SCAVENGER;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DECOMPOSITION; SYNTHESIS;

EID: 0037716294 PISSN: 1434193X EISSN: None Source Type: Journal
DOI: 10.1002/ejoc.200300215 Document Type: Article

Times cited : (76)

References (43)

1
- 0038567454
- [1a] S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968; Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
- (2003) Angew. Chem. , vol.115 , pp. 1944-1968
- Connon, S.J.¹ Blechert, S.²

2
- 0038215596
- [1a] S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968; Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1900-1923

3
- 0001254536
- [1b] S. E. Gibson, S. P. Keen, Top. Organomet. Chem. 1998, 155-181.
- (1998) Top. Organomet. Chem. , pp. 155-181
- Gibson, S.E.¹ Keen, S.P.²

4
- 0035808923
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (2001) Tetrahedron Lett. , vol.42 , pp. 1175-1178
- Pietraszuk, C.¹ Fisher, H.² Kujawa, M.³ Marciniec, B.⁴

5
- 0006402256
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (2000) Org. Lett. , vol.2 , pp. 551-553
- Ahmed, M.¹ Arnauld, T.² Barret, A.G.M.³ Braddock, D.C.⁴ Flack, K.⁵ Procopiou, P.A.⁶

6
- 0034639441
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 58-71
- Blackwell, H.E.¹ O'Leary, D.J.² Chatterjee, A.K.³ Washenfelder, R.A.⁴ Bussmann, D.A.⁵ Grubbs, R.H.⁶

7
- 0000904154
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (2000) Org. Lett. , vol.2 , pp. 327-330
- Seshadri, H.¹ Lovely, C.J.²

8
- 0033597320
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (1999) Tetrahedron Lett. , vol.40 , pp. 3305-3308
- Hu, Y.J.¹ Roy, R.²

9
- 33748666441
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2485-2499
- Biagini, S.C.G.¹ Gibson, S.E.² Keen, S.P.³

10
- 0033516679
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (1999) Tetrahedron , vol.55 , pp. 8155-8167
- Kinoshita, A.¹ Sakakibara, N.² Mori, M.³

11
- 0033531371
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (1999) Chem. Commun. , pp. 237-238
- Stragies, R.¹ Schuster, M.² Blechert, S.³

12
- 0038545118
- For examples of ene-ene CM catalysed by 1 see: [2a] C. Pietraszuk, H. Fisher, M. Kujawa, B. Marciniec, Tetrahedron Lett. 2001, 42, 1175-1178. [2b] M. Ahmed, T. Arnauld, A. G. M. Barret, D. C. Braddock, K. Flack, P. A. Procopiou, Org. Lett. 2000, 2, 551-553. [2c] H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. [2d] H. Seshadri, C. J. Lovely, Org. Lett. 2000, 2, 327-330. [2e] Y. J. Hu, R. Roy, Tetrahedron Lett. 1999, 40, 3305-3308. [2f] S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 2485-2499. For examples of ene-yne CM catalysed by 1 see: [2g] A. Kinoshita, N. Sakakibara, M. Mori, Tetrahedron 1999, 55, 8155-8167. [2h] R. Stragies, M. Schuster, S. Blechert, Chem. Commun. 1999, 237-238. [2i] S. C. Schürer, S. Blechert, Synlett 1999, 1879-1882.
- (1999) Synlett , pp. 1879-1882
- Schürer, S.C.¹ Blechert, S.²

13
- 0038002181
- [3a] A. Fürstner, O. R. Thiel, C. W. Lehmann, Organometallics 2002, 21, 331-335.
- (2002) Organometallics , vol.21 , pp. 331-335
- Fürstner, A.¹ Thiel, O.R.² Lehmann, C.W.³

14
- 0000466073
- [3b] L. Jafarpour, A. C. Hillier, S. P. Nolan, Organometallics 2002, 21, 442-444.
- (2002) Organometallics , vol.21 , pp. 442-444
- Jafarpour, L.¹ Hillier, A.C.² Nolan, S.P.³

15
- 0033582991
- [3c] M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
- (1999) Tetrahedron Lett. , vol.40 , pp. 2247-2250
- Scholl, M.¹ Trnka, T.M.² Morgan, J.P.³ Grubbs, R.H.⁴

16
- 0037050473
- [4a] J. P. Morgan, C. Morrill, R. H. Grubbs, Org. Lett. 2002, 4, 67-70.
- (2002) Org. Lett. , vol.4 , pp. 67-70
- Morgan, J.P.¹ Morrill, C.² Grubbs, R.H.³

17
- 0001754263
- [4b] A. K. Chatterjee, D. P. Sanders, R. H. Grubbs, Org. Lett. 2002, 4, 1939-1942.
- (2002) Org. Lett. , vol.4 , pp. 1939-1942
- Chatterjee, A.K.¹ Sanders, D.P.² Grubbs, R.H.³

18
- 0001322119
- [4c] T. L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317-1319; Angew. Chem. Int. Ed. 2001, 40, 1277-1279.
- (2001) Angew. Chem. , vol.113 , pp. 1317-1319
- Choi, T.L.¹ Chatterjee, A.K.² Grubbs, R.H.³

19
- 0035794963
- [4c] T. L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317-1319; Angew. Chem. Int. Ed. 2001, 40, 1277-1279.
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1277-1279

20
- 0035940104
- [4d] M. Lera, C. J. Hayes, Org. Lett. 2001, 3, 2765-2768.
- (2001) Org. Lett. , vol.3 , pp. 2765-2768
- Lera, M.¹ Hayes, C.J.²

21
- 0034661914
- [4e] R. Stragies, U. Voigtmann, S. Blechert, Tetrahedron Lett. 2000, 41, 5465-5468.
- (2000) Tetrahedron Lett. , vol.41 , pp. 5465-5468
- Stragies, R.¹ Voigtmann, U.² Blechert, S.³

22
- 0034685462
- [4f] A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783-3784.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3783-3784
- Chatterjee, A.K.¹ Morgan, J.P.² Scholl, M.³ Grubbs, R.H.⁴

23
- 0034609694
- [4g] J. P. Morgan, R. H. Grubbs, Org. Lett. 2000, 2, 3153-3155.
- (2000) Org. Lett. , vol.2 , pp. 3153-3155
- Morgan, J.P.¹ Grubbs, R.H.²

24
- 0033518063
- [4h] A. K. Chatterjee, R. H. Grubbs, Org. Lett. 1999, 1, 1751-1753.
- (1999) Org. Lett. , vol.1 , pp. 1751-1753
- Chatterjee, A.K.¹ Grubbs, R.H.²

25
- 0001461838
- [5a] D. L. Wright, L. C. Usher, M. Esterella-Jimenez, Org. Lett. 2001, 3, 4275-4277.
- (2001) Org. Lett. , vol.3 , pp. 4275-4277
- Wright, D.L.¹ Usher, L.C.² Esterella-Jimenez, M.³

26
- 0034676688
- [5b] S. Gessler, S. Randl, S. Blechert, Tetrahedron Lett. 2000, 41, 9973-9976.
- (2000) Tetrahedron Lett. , vol.41 , pp. 9973-9976
- Gessler, S.¹ Randl, S.² Blechert, S.³

27
- 0032940083
- Except for: [5c] O. M. Blanco, L. Castedo, Synlett 1999, 557-558.
- (1999) Synlett , pp. 557-558
- Blanco, O.M.¹ Castedo, L.²

28
- 0034804462
- [6a] S. Randl, N. Buschmann, S. J. Connon, S. Blechert, Synlett 2001, 1547-1550.
- (2001) Synlett , pp. 1547-1550
- Randl, S.¹ Buschmann, N.² Connon, S.J.³ Blechert, S.⁴

29
- 0035108849
- [6b] S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430-432.
- (2001) Synlett , pp. 430-432
- Randl, S.¹ Gessler, S.² Wakamatsu, H.³ Blechert, S.⁴

30
- 0034734340
- S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 8168-8179
- Garber, S.B.¹ Kingsbury, J.S.² Gray, B.L.³ Hoveyda, A.H.⁴

31
- 0343131928
- [8a] O. Brümmer, A. Rückert, S. Blechert, Chem. Eur. J. 1997, 3, 441-446.
- (1997) Chem. Eur. J. , vol.3 , pp. 441-446
- Brümmer, O.¹ Rückert, A.² Blechert, S.³

32
- 0001193782
- [8b] W. E. Crowe, D. R. Goldberg, J. Am. Chem. Soc. 1995, 117, 5162-5163.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5162-5163
- Crowe, W.E.¹ Goldberg, D.R.²

33
- 0037161790
- T. M. Cameron, A. S. Gamble, K. A. Abboud, J. M. Boncella, Chem. Commun. 2002, 1148-1149.
- (2002) Chem. Commun. , pp. 1148-1149
- Cameron, T.M.¹ Gamble, A.S.² Abboud, K.A.³ Boncella, J.M.⁴

34
- 0038238936
- J. A. Love, J. P. Morgan, T. M. Trnka, R. H. Grubbs, Angew. Chem. 2002, 114, 4207-4209; Angew. Chem. Int. Ed. 2002, 41, 4035-4037.
- (2002) Angew. Chem. , vol.114 , pp. 4207-4209
- Love, J.A.¹ Morgan, J.P.² Trnka, T.M.³ Grubbs, R.H.⁴

35
- 85034336744
- J. A. Love, J. P. Morgan, T. M. Trnka, R. H. Grubbs, Angew. Chem. 2002, 114, 4207-4209; Angew. Chem. Int. Ed. 2002, 41, 4035-4037.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4035-4037

36
- 0000335507
- [11a] J. Huang, H. J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5375-5380.
- (1999) Organometallics , vol.18 , pp. 5375-5380
- Huang, J.¹ Schanz, H.J.² Stevens, E.D.³ Nolan, S.P.⁴

37
- 0032564844
- [11b] D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1627-1628
- Lynn, D.M.¹ Mohr, B.² Grubbs, R.H.³

38
- 0001467672
- [11c] M. S. Sanford, L. M. Henling, R. H. Grubbs, Organometallics 1998, 17, 5384-5389.
- (1998) Organometallics , vol.17 , pp. 5384-5389
- Sanford, M.S.¹ Henling, L.M.² Grubbs, R.H.³

39
- 0030994105
- [11d] E. L. Dias, S. T. Nguyen, R. H Grubbs, J. Am. Chem. Soc. 1997, 119, 3887-3897.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 3887-3897
- Dias, E.L.¹ Nguyen, S.T.² Grubbs, R.H.³

40
- 0033578944
- M. Ulman, R. H. Grubbs, J. Org. Chem. 1999, 64, 7202-7207.
- (1999) J. Org. Chem. , vol.64 , pp. 7202-7207
- Ulman, M.¹ Grubbs, R.H.²

41
- 3743093401
- E. L. Dias, R. H. Grubbs, Organometallics 1998, 17, 2758-2767.
- (1998) Organometallics , vol.17 , pp. 2758-2767
- Dias, E.L.¹ Grubbs, R.H.²

42
- 0034660543
- M. Ulman, T. R. Belderrain, R. H. Grubbs, Tetrahedron Lett. 2000, 41, 4689-4693.
- (2000) Tetrahedron Lett. , vol.41 , pp. 4689-4693
- Ulman, M.¹ Belderrain, T.R.² Grubbs, R.H.³

43
- 0038567453
- note
- For studies concerning the thermal stability of NHC-coordinated ruthenium complexes see ref 11a.

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